Substituted arylalkanoic acid derivatives and use thereof

ABSTRACT

A compound represented by the formula (I): 
     
       
         
         
             
             
         
       
     
     [In the formula, Link represents a saturated or unsaturated straight hydrocarbon chain having 1 to 3 carbon atoms, C 2  to C 6  in the aromatic ring (E) independently represent a ring-constituting carbon atom, one of the ring-constituting carbon atoms may be replaced with V, V represents nitrogen atom, or carbon atom substituted with Zx, Zx represents a saturated alkyl group having 1 to 4 carbon atoms and the like, Rs represents -D-Rx etc., D represents a single bond, oxygen atom and the like, Rx represents a saturated alkyl group having 3 to 8 carbon atoms and the like, AR represents a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or a heterocyclic ring, and Y represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms and the like] or a salt thereof. A compound having prostaglandin production-suppressing action and leukotriene production-suppressing action is provided.

This application is a Divisional of co-pending application Ser. No. 10/568,185 filed on Feb. 13, 2006 and for which priority is claimed under 35 U.S.C. § 120. application Ser. No. 10/568,185 is the national phase of PCT International Application No. PCT/JP2004/011953 filed on Aug. 13, 2004 under 35 U.S.C. § 371. This application also claims priority to U.S. Provisional Application No. 60/495,734, filed Aug. 18, 2003 under 35 U.S.C. § 119(e) and JP2003-293590, filed in Japan on Aug. 14, 2003 under 35 U.S.C. § 119(a). The entire contents of each of the above-identified applications are hereby incorporated by reference.

FIELD OF THE INVENTION

The present invention relates to a novel substituted arylalkanoic acid derivative. More specifically, the present invention relates to a substituted arylalkanoic acid derivative having an action as a medicament and a synthetic intermediate of said compound.

BACKGROUND ART

Various kinds of prostaglandins and various kinds of leukotrienes are produced in the bodies of mammals in response to variety of stimuli such as inflammatory stimuli and physical stimuli.

Both of prostaglandins and leukotrienes are metabolites of arachidonic acid, and they are physiologically active substances referred to as lipid mediators, and they cause various physiological responses of mammals by binding to receptors expressed on surfaces of various cells or in the cells.

Arachidonic acid is produced from a phospholipid as a substrate, such as phosphatidylcholine which is a cell membrane component, with the aid of an enzymatic activity of phospholipase A₂ (PLA₂).

Arachidonic acid produced by the action of PLA₂ is converted into prostaglandin (PG) H₂ with the aid of an enzymatic activity of constitutive type cyclooxygenase (COX) 1 or inducible type COX-2, and further converted into PGE₂, PGD₂, PGF₂ α, PGI₂, thromboxane (TX) A₂ and the like with the aid of each synthetic enzyme. Further, arachidonic acid is also metabolized by the action of 5-lipoxygenase (5-LO) and thereby converted to leukotriene (LT) A₄, and further converted to LTB₄, LTC₄, LTD₄, LTE₄ and the like by the enzymatic activities of LTA₄ hydrolase, LTC₄ synthase, glutathione S-transferase and the like [Goodman & Gilman, Pharmacological Basis of Therapeutics, 9th edition, p. 801, 1999 (Hirokawa Shoten); Funk, C. D., SCIENCE, vol. 294, p. 1871, 2001].

Prostaglandins bind to each specific receptor to cause inflammatory reactions such as fervescence, enhancement of vascular permeability, vasodilation, swelling and pain, bronchial smooth muscle contraction, platelet aggregation, tumor cell proliferation, enhancement of bone resorption, nerve cell degeneration and the like, and thus play important roles in expression of symptoms or pathological formation for various diseases.

Leukotrienes are physiologically active substances which bind to each specific receptor to cause inflammatory reactions such as excessive accumulation of leucocytes and enhancement of vascular permeability, smooth muscle contraction, mucus secretion, proliferation of tumor cells and the like, and thus play important roles in expression of symptoms or pathological formation for various diseases.

Although inflammatory reactions themselves are essential reactions for living bodies to survive when they face pathogenic substances and affections, they are sometimes excessively caused or continue without any reason for providing evident benefit under certain situations or in certain diseases [Goodman & Gilman, Pharmacological Basis of Therapeutics, 9th edition, p. 827, 1999 (Hirokawa Shoten)]. The condition of living body referred to in this specification wherein an acute or chronic inflammatory reaction is observed means a condition that an excessive or unbeneficial acute or temporary inflammatory reaction or chronic and persistent inflammatory reaction is caused. Further, an inflammatory reaction refers to a series of events caused by stimuli, for example, physical hazards such as heat, infective substances, ischemia, antigen/antibody reaction and the like, and it is accompanied by flare, swelling, hyperalgesia, algesic onset and the like as well-known macroscopic clinical symptoms. It is known that, as histological mechanisms for these reactions, vasodilation, enhancement of vascular permeability, infiltration of leucocytes and phagocytes, histological decomposition and fibrosing and the like are caused [Goodman & Gilman, Pharmacological Basis of Therapeutics, 9th edition, p. 827, 1999 (Hirokawa Shoten)]. It is known that many of these histological reactions are caused by prostaglandins and/or leukotrienes, and prostaglandins and/or leukotrienes plays important roles in inflammatory reactions.

For example, it was reported that, in a pathological tissue of rheumatoid arthritis, which is an autoimmune and chronic inflammatory disease, expression of COX-2 and production of PGE₂ and TXA₂ as well as expression of 5-LO and production of LTB₄ were observed (Bonnet et al., Prostaglandins, 1995, vol. 50, p. 127), and in a mouse deficient in FLAP, which is a protein required for activation of 5-LO, symptom of collagen-induced arthritis, which is a pathological model of chronic rheumatoid arthritis, was milder compared with that in a wild-type mouse (Griffiths et al., J. Exp. Med., 1997, vol. 185, p. 1123), and thus it has been suggested that prostaglandins and leukotrienes play important roles in the pathological formation of chronic rheumatoid arthritis.

It was reported that, in a pathological tissue of bronchial asthma, one of chronic allergic diseases, excessive production of PGD₂ and TXA₂ as well as excessive production of LTC₄ and LTD₄ were observed (Wenzel et al., Am Rev. Respir. Dis., 1990, vol. 142, p. 112), and an airway hypersensitive reaction, which is a pathological model of bronchial asthma, was unlikely to occur in a PGD₂ receptor-deficient mouse (Matsuoka et al., SCIENCE, vol. 287, p. 2013, 2000). Thus, it has been demonstrated that roles of prostaglandins and leukotrienes are important in bronchial asthma.

In a cerebral tissue after ischemic reperfusion, expression of COX-2 increased, and concentrations of PGE₂ and TXA₂ increased, whereas activity of 5-LO increased, and production amount of LTC₄ increased (Ohtsuki et al., Am. J. Physiol., 1995, vol. 268, p. 1249). Thus, it is known that prostaglandins and leukotrienes play important roles in formation of infarct that is accepted as an ischemic reperfusion injury.

It has been revealed that, in a pathological tissue of Alzheimer's disease, one of the diseases with neurodegeneration, the COX activity and 5-LO activity increased, prostaglandins and leukotrienes cause formation of the β-amyloid protein, one of the pathogenic substances of Alzheimer's disease, and further cause degeneration of nerve cells (Sugaya et al., Jpn. J. Pharmacol., 2000, vol. 82, p. 85), and thus it is believed that prostaglandins and leukotrienes play important roles in the formation of neurodegenerative diseases such as Alzheimer's disease.

Furthermore, for example, it was reported that, in a pathological tissue of colon cancer, COX and 5-LO were expressed, and amounts of production of prostaglandins and leukotrienes were increased (Dreyling et al., Biochim. Biophys. Acta., 1986, vol. 878, p. 184), and leukotriene caused increase in colon cancer cells (Qiao et al., Biochim. Biophys. Acta, 1995, vol. 1258, p. 215; Hong et al., Cancer Res., 1999, vol. 59, p. 2223). Thus, it is believed that prostaglandins and leukotrienes play important roles also in tissues of large bowel cancer.

Involvement of prostaglandins and/or leukotrienes in diseases and pathological conditions is not limited to those diseases exemplified above, and it has been demonstrated that prostaglandins and/or leukotrienes are involved in variety of conditions, various diseases, or various pathological conditions where acute or chronic inflammatory reactions are observed and their roles are important.

For the above reason, various prostaglandin production suppressors or leukotriene production suppressors are used as agents for prophylactic or therapeutic treatment of conditions, various diseases or pathological conditions where an acute or chronic inflammatory reaction is recognized. Various non-steroidal anti-inflammatory drugs (NSAIDS) as medicaments having a prostaglandin production-suppressing action are available and used as therapeutic agents for chronic rheumatoid arthritis and osteoarthritis, antiphlogistic-analgesic agents for injury and the like, prophylactic agents for cerebral infarction or myocardial infarction, prophylactic agents for colon polyposis and the like. However, the class of NSAIDS suppress only production of prostaglandins, and as a result, they increase amounts of production of leukotrienes, and exhibit side effects such as asthmatic attack and gastrointestinal injury as well as renal disturbance. Furthermore, a difference between an effective dose and a dose inducing the side effects is small in these NSAIDS, and no satisfactory agent is available from a viewpoint of therapeutic effect. A 5-LO inhibitor is available which is described in European Patent No. 279263 as a medicament having a leukotriene production-suppressing action, and the inhibitor is known as a prophylactic agent for asthma. However, since the agent causes side effects such as hepatic disorder, its dosage is limited, and the agent is not satisfactory also from a viewpoint of therapeutic effect. Since steroid agents suppress production of both of prostaglandins and leukotrienes, they are used as prophylactic agents or therapeutic agents for conditions of living bodies, various diseases and pathological conditions where various acute or chronic inflammatory reactions are observed. However, their actions are not limited to the lipid mediator production-suppressing action, and they exhibit severe side effects such as induction and exacerbation of infectious diseases due to the immunosuppression action, growth retardation due to normal cell antiproliferative activity, anetoderma and peptic ulcer. Therefore, their uses are limited.

Furthermore, for the above reasons, it is considered that compounds, that suppress the production of both of prostaglandins and leukotrienes and have reduced side effect, are effective as therapeutic agents or prophylactic agents for such conditions of living bodies, diseases or pathological conditions in mammals as described above, and methods of using such compounds together with medicaments available at present are more effective therapeutic or prophylactic methods. Therefore, development of compounds suppressing the production of both of prostaglandins and leukotrienes, and manufacture of pharmaceutical preparations thereof are strongly desired.

As compounds structurally similar to the compounds of the present invention, for example, biphenyl-5-alkanoic acid derivatives and use thereof are described in WO99/19291. However, the moiety of these compounds that corresponds to “AR” included in the formula (I) of the compounds of the present invention is phenyl group, and thus structural features of the above compounds are different. Further, biaryl phospholipase A² inhibitors are described in U.S. Pat. No. 5,391,817 [Japanese Patent Unexamined Publication (Kokai) No. 7-22399]. However, the moiety of these compounds that corresponds to “AR” included in the formula (I) of the compounds of the present invention is only defined to be phenyl group, and thus the structural features of the above compounds are different. Bicyclic heterocyclic compounds are described in WO00/35886 as protease inhibitors. However, the substituents of these compounds on the moiety that corresponds to “AR” included in the formula (I) of the compounds of the present invention are different, and further, the publication is completely silent about whether or not the compounds described in the above patent document have any prostaglandin production-suppressing action or leukotriene production-suppressing action.

[Patent document 1] WO99/19291 [Patent document 2] U.S. Pat. No. 5,391,817 [Patent document 3] WO00/35886

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide a novel compound having superior prostaglandin production-suppressing action and leukotriene production-suppressing action. Another object of the present invention is to provide a compound for prophylactic and/or therapeutic treatment of various inflammatory diseases, autoimmune diseases, allergic diseases, pain and fibrosis in mammals caused by lipid mediators. A further object of the present invention is to provide a pharmaceutical composition containing such a compound. A still further object of the present invention is to provide an intermediate for the production of the compound. These objects and other objects as well as advantages of the present invention will be apparent for those skilled in the art from the following descriptions.

In order to achieve the aforementioned objects, the inventors of the present invention conducted various researches. As a result, they found that the substituted arylalkanoic acid derivatives represented by the following general formula, which are novel compounds, had superior prostaglandin production-suppressing action and leukotriene production-suppressing action, and thus accomplished the present invention.

The present invention is embodied by, for example, those described in the following (1) to (191).

(1) A compound represented by the formula (I):

[In the formula, Link represents a saturated or unsaturated straight hydrocarbon chain having 1 to 3 carbon atoms.

C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) independently represent a ring-constituting carbon atom. One of the ring-constituting carbon atoms to which Rs and AR do not bind may be replaced with V.

V represents nitrogen atom, or carbon atom substituted with Zx. Zx represents a linear or branched saturated alkyl group having 1 to 4 carbon atoms, fluorine atom, chlorine atom, bromine atom, nitro group, —OR⁹, or —N(Rn¹)(Rn²). R⁹ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qp, wherein A⁶ represents a single bond or methylene, Qp represents phenyl group, and the phenyl group may be substituted with one of T¹ or two or more of the same or different T¹. T¹ represents a linear or branched saturated alkyl group having 1 to 4 carbon atoms, hydroxyl group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, nitro group, an alkoxy group having 1 to 4 carbon atoms, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Rn¹ represents hydrogen atom or a linear or branched saturated alkyl group having 1 to 4 carbon atoms, Rn² has the same meaning as Rn¹, or represents —COR²³ or —SO₂R²⁴, or binds to Rn¹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group. R²³ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, —O-A⁶-Qp, or —N(R²⁵)(R²⁶). R²⁵ represents hydrogen atom, or a linear or branched saturated alkyl group having 1 to 4 carbon atoms. R²⁶ has the same meaning as R²⁵, or binds to R²⁵ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group. R²⁴ represents a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms.

Rs represents -D-Rx or —N(Ry)(Rz).

D represents a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —C(O).

Rx represents a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or represents Ra represented by the following formula:

R¹(CH₂)_(k)—  (Ra)

Rb represented by the following formula:

or Rc represented by the following formula:

k in Ra represents 0 or an integer of 1 to 3. R¹ represents a saturated cyclic alkyl group having 3 to 7 carbon atoms, or a condensed saturated cyclic alkyl group having 6 to 8 carbon atoms, and R¹ may be substituted with one of lower alkyl group having 1 to 4 carbon atoms or two or more of the same or different lower alkyl groups having 1 to 4 carbon atoms. Q in Rb represents a partially unsaturated or completely unsaturated monocyclic or condensed bicyclic carbon ring or a heterocyclic ring (q), and binds to A² at an arbitrary position. The heterocyclic ring (q) contains the same or different 1 to 4 ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom. A¹ represents a single bond or an alkylene (a) having 1 to 3 carbon atoms, and the alkylene (a) may be substituted with a lower alkyl group having 1 to 4 carbon atoms or phenyl group. A² represents a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)— (provided that when A² represents oxygen atom, sulfur atom, —S(O)—, —S(O)₂— or —N(R⁴)—, A¹ represents ethylene or trimethylene). R² and R³ independently represent hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, —OR⁵, —N(R⁶)(R⁶′), —NHCOR⁷, —NHSO₂R⁸, or -A⁶-Qa, or they bind to each other to represent methylenedioxy group. Qa represents a partially unsaturated or completely unsaturated monocyclic or condensed bicyclic carbon ring or a heterocyclic ring (qa), binds to A⁶ at an arbitrary position on the ring, and may be substituted with one of T¹ or two or more of the same or different T¹. The heterocyclic ring (qa) contains the same or different 1 to 4 ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom. R⁴ and R⁶ independently represent hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. R⁵ and R⁷ independently represent hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qa. R⁸ represents a lower alkyl group having 1 to 4 carbon atoms. R⁶′ has the same meaning as R⁶, or binds to R⁶ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group. p in Rc represents an integer of 2 to 4. A⁴ represents a single bond, methylene, or ethylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or Qa. Re represents an alkyl group having 1 to 8 carbon atoms, -A⁶-Qa, —(CH₂)_(i)R¹⁴, —OR²⁸, —SR²⁸, or —N(R²⁹)(R³⁰). i represents an integer of 1 to 3, R¹⁴ represents hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, carboxyl group, or an N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms. R²⁸ represents an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qa. R²⁹ represents an alkyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or -A⁶-Qa. R³⁰ represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or binds to R²⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group.

Rz has the same meaning as Rx, or Rz represents methyl group, ethyl group, or -A⁵-Re. Ry represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qp, or Ry may bind to Rz to form, together with a nitrogen atom to which they bind, a saturated or unsaturated 3 to 7-membered nitrogen-containing cyclic group, wherein said nitrogen-containing cyclic group may optionally be substituted with one or two lower alkyl groups having 1 to 4 carbon atoms wherein said two alkyl groups may be the same or different.

AR represents a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or a heterocyclic ring (ar), and may be substituted with one of Xa or two or more of the same or different Xa. The heterocyclic ring (ar) contains the same or different 1 to 4 ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom. Xa represents a linear or branched saturated alkyl group having 1 to 4 carbon atoms, a saturated cyclic alkyl group having 3 to 7 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, —(CH₂)_(i)R¹⁴, —OR¹⁰, —N(R¹¹)(R¹²), —SO₂R¹³, or —COR²⁷. R¹⁰ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or —(CH₂)_(i)R¹⁴. R¹¹ represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. R¹² represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, —COR¹⁵, or —SO₂R¹⁶, or binds to R¹¹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group. R¹⁵ represents a lower alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, amino group, a mono- or dialkylamino group having 1 to 4 carbon atoms, or -A⁶-Qa. R¹³ and R¹⁶ independently represent a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms. R²⁷ represents hydrogen atom, hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms.

Y represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, —(CH₂)_(m)N(R¹⁸)(R¹⁹), or C(R²⁰)₂OC(O)A³R²¹. Symbol m represents an integer of 2 or 3. R¹⁸ is the same as R¹⁹, or binds to R¹⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group. R¹⁹ represents methyl group, ethyl group, or propyl group. R²⁰ represents hydrogen atom, methyl group, ethyl group, or propyl group. R²¹ represents a lower alkyl group having 1 to 4 carbon atoms, a cyclic saturated alkyl group having 3 to 6 carbon atoms, or phenyl group, and A³ represents a single bond, or oxygen atom. This compound may sometimes be hereinafter referred to simply as “Compound (I)” of the present invention.”] or a salt thereof.

(1-2) The compound or salt thereof according to (1), wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 1 to 3, Rz has the same meaning as that of Rx or represents -A⁵-Re when Rs is —N(Ry)(Rz), and Ry is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or A⁶-Qp, or Ry binds to Rz to form, together with a nitrogen atom to which they bind, a saturated or unsaturated 3 to 7-membered nitrogen-containing cyclic group. (2) The compound or salt thereof according to (1) or (1-2) mentioned above, wherein, in the formula (I), AR binds to any atom among C² and C³ in the aromatic ring (E). (3) The compound or salt thereof according to any one of (1) to (2) mentioned above, wherein, in the formula (I), n is an integer of 2 (the description of “according to any one of (1) to (2)” includes (1-2) mentioned above, and the same or similar description should be construed in the same manner hereinafter in the specification). (4) The compound or salt thereof according to any one of (1) to (3) mentioned above, wherein, in the formula (I), AR is a residue of naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, dihydro-2H-isoquinoline, cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole, dihydro-3H-benzoxazole, phthalazine, [1,8]naphthalidine, [1,5]naphthalidine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrazolo[4,3-b]pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[3,4-b]pyridine, [1,2,4]triazolo[4,3-a]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, 1H-thieno[3,2-c]pyrazole, benzo[d]isoxazole, benzo[c]isoxazole, indolizine, 1,3-dihydroindole, 1H-pyrazolo[3,4-d]thiazole, 2H-isoindole, [1,2,4]triazolo[1,5-a]pyrimidine, 1H-pyrazolo[3,4-b]pyrazine, 1H-imidazo[4,5-b]pyrazine, 7H-purine, or 4H-chromene (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa). (5) The compound or salt thereof according to any one of (1) to (3) mentioned above, wherein, in the formula (I), AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa). (6) The compound or salt thereof according to any one of (1) to (3) mentioned above, wherein, in the formula (I), AR is a residue of naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, or dihydro-2H-isoquinoline (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa). (7) The compound or salt thereof according to any one of (1) to (3) mentioned above, wherein, in the formula (I), AR is a residue of cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole, dihydro-3H-benzoxazole, phthalazine, [1,8]naphthalidine, [1,5]naphthalidine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrazolo[4,3-b]pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[3,4-b]pyridine, [1,2,4]triazolo[4,3-a]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, 1H-thieno[3,2-c]pyrazole, benzo[d]isoxazole, benzo[c]isoxazole, indolizine, 1,3-dihydroindole, 1H-pyrazolo[3,4-d]thiazole, 1H-pyrazolo[3,4-d]thiazole, 2H-isoindole, [1,2,4]triazolo[1,5-a]pyrimidine, 1H-pyrazolo[3,4-b]pyrazine, 1H-imidazo[4,5-b]pyrazine, 7H-purine, or 4H-chromene (the aforementioned residue may have one of Xa or two or more of the same or different Xa). (8) The compound or salt thereof according to any one of (1) to (7) mentioned above, wherein, in the formula (I), Rs is -D-Rx or —N(Ry)(Rz), D is a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—, Rx is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra, Rb, or Rc, k in Ra is 0 or an integer of 1 to 3, R¹ is a saturated cyclic alkyl group having 3 to 7 carbon atoms or a condensed saturated cyclic alkyl group having 6 to 8 carbon atoms, R¹ may be substituted with one of lower alkyl group having 1 to 4 carbon atoms or two or more of the same or different lower alkyl groups having 1 to 4 carbon atoms, Q in Rb is phenyl group, thienyl group, furyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, 4H-chromenyl group, dihydrobenzodioxyl group, benzoisoxazolyl group, pyrrolopyridinyl group, pyrazolopyridinyl group, triazolopyridinyl group, thienopyridinyl group, thienopyrazolyl group, 1,3-dihydrobenzimidazole group, dihydro-3H-benzoxazole group, or dihydro-3H-benzothiazole group (the aforementioned groups binds to A² at an arbitrary position), A¹ is a single bond or an alkylene (a) having 1 to 3 carbon atoms, the alkylene (a) may be substituted with a lower alkyl group having 1 to 4 carbon atoms or phenyl group, A² is a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)— (provided that when A² represents oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)—, A¹ represents ethylene or trimethylene), R² and R³ independently represent hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, —OR⁶, —N(R⁶)(R⁶′), —NHCOR⁷, —NHSO₂R⁸, or -A⁶-Qa, or they bind to each other to represent methylenedioxy group, Qa is phenyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, or indazolyl group (these groups may be substituted with one of T¹ or two or more of the same or different T¹, and bind to A⁶ at an arbitrary position on the ring), R⁴ and R⁶ independently represent hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R⁵ and R⁷ independently represent hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qa, R⁸ is a lower alkyl group having 1 to 4 carbon atoms, R⁶′ has the same meaning as R⁶, or binds to R⁶ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group, p in Rc is an integer of 2 to 4, A⁴ is a single bond or methylene or ethylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or Qa, Re is an alkyl group having 1 to 8 carbon atoms, -A⁶-Qa, —(CH₂)_(i)R¹⁴, —OR²⁸, —SR²⁸, or —N(R²⁹)(R³⁰), i is an integer of 1 to 3, R¹⁴ is hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, carboxyl group, or an N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms, R²⁸ is an alkyl group having 1 to 8 carbon atoms or -A⁶-Qa, R²⁹ is an alkyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or -A⁶-Qa group, R³⁰ is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or binds to R²⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group, Rz has the same meaning as Rx, or is -A⁵-Re, and Ry is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qp, or binds to Rz to form a saturated or unsaturated nitrogen-containing cyclic substituent having 3 to 7 atoms together with nitrogen atom to which they binds. (9) The compound or salt thereof according to any one of (1) to (8) mentioned above, wherein, in the formula (I), among C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E), one ring-constituting atom to which Rs or AR does not bind is replaced with nitrogen atom. (10) The compound or salt thereof according to any one of (1) to (8) mentioned above, wherein, in the formula (I), among C², C³, C⁴, C⁵, or C⁶ in the aromatic ring (E), one ring-constituting atom to which Rs or AR does not bind is replaced with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² represents a substituent other than hydrogen atom). (11) The compound or salt thereof according to (1) or (10) mentioned above, wherein, in the formula (I), Rs is —O-Rx. (12) The compound or salt thereof according to any one of (1) to (11) mentioned above, wherein, in the formula (I), Rs is —O-Rc. (13) The compound or salt thereof according to any one of (1) to (10) mentioned above, wherein, in the formula (I), Rs is —N(Ry)(Rz). (14) The compound or salt thereof according to any one of (1) to (10) mentioned above, wherein, in the formula (I), Rs is -D-Rx, and D is a single bond, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (15) The compound or salt thereof according to any one of (1) to (10) mentioned above, wherein, in the formula (I), Rs is —S-Rx. (16) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds at the position of C² in the aromatic ring (E), and Rs binds to one of the ring-constituting carbon atoms C³, C⁴, and C⁵. (17) The compound or salt thereof according to (16) mentioned above, wherein, in the formula (I), Rs is —O-Rx, and no ring-constituting carbon atom in the aromatic ring (E) is replaced with V. (18) The compound or salt thereof according to (16) or (17) mentioned above, wherein, in the formula (I), n is an integer of 2, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (19) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds at the position of C² in the aromatic ring (E), Rs binds to one of ring-constituting carbon atoms C³, C⁴ and C⁵, Rs is —O-Rx, Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and all of C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) are not replaced with V. (20) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds at the position of C² in the aromatic ring (E), Rs binds to one of ring-constituting carbon atoms C³, C⁴ and C⁵, Rs is —O-Rx, Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and all of C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) are not replaced with V. (21) The compound or salt thereof according to any one of (16) to (20) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (22) The compound or salt thereof according to any one of (16) to (21) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, a methylene group substituted with methyl group or ethyl group, or unsubstituted methylene group, or an ethylene group substituted with methyl group or ethyl group, or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (23) The compound or salt thereof according to any one of (16) to (22) mentioned above, wherein, in the formula (I), Rx-D- binds at the position of C³ in the aromatic ring (E). (24) The compound or salt thereof according to any one of (16) to (22) mentioned above, wherein, in the formula (I), Rx-D- binds at the position of C⁴ in the aromatic ring (E). (25) The compound or salt thereof according to any one of (16) to (22) mentioned above, wherein, in the formula (I), Rx-D- binds at the position of C⁵ in the aromatic ring (E). (26) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3, AR binds to C², Rs binds to one of the ring-constituting carbon atoms C³, C⁴, and C⁵, a ring-constituting atom among C³, C⁴, and C⁶ to which Rs does not bind may be replaced with V,

V is nitrogen atom or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is -D-Rx or —N(Ry)(Rz), D is oxygen atom or sulfur atom, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, and A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). Symbol p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with nitrogen atom to which they binds,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and Y is hydrogen atom, methyl group or ethyl group.

(27) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C² is carbon atom to which AR binds, C³ is carbon atom to which Rs binds, C⁴ may be replaced with V, C⁵ and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(28) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C² is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ may be replaced with V, C³ and C⁶ represents an unsubstituted ring-constituting carbon atom,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(29) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), and Rs binds to C⁵ or C⁶ in the aromatic ring (E). (30) The compound or salt thereof according to (29) mentioned above, wherein, in the formula (I), Rs is —O-Rx, and all of C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) are not replaced with V. (31) The compound or salt thereof according to (29) or (30) mentioned above, wherein, in the formula (I), n is an integer of 2, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (32) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to the ring-constituting carbon atom C⁵ or C⁶ in the aromatic ring (E), Rs is —O-Rx, Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and all of C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) are not replaced with V. (33) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to the ring-constituting carbon atom C⁵ or C⁶ in the aromatic ring (E), Rs is —O-Rx, Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and all of C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) are not replaced with V. (34) The compound or salt thereof according to any one of (29) to (33) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group., methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (35) The compound or salt thereof according to any one of (29) to (34) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (36) The compound or salt thereof according to any one of (29) to (35) mentioned above, wherein, in the formula (I), R⁵ binds at the position of C⁵ in the aromatic ring (E). (37) The compound or salt thereof according to any one of (29) to (35) mentioned above, wherein, in the formula (I), Rs binds at the position of C⁶ in the aromatic ring (E). (38) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁶ is carbon atom to which Rs binds, C², C⁴ and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(39) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), and C⁶ is replaced with V. (40) The compound or salt thereof according to (39) mentioned above, wherein, in the formula (I), n is an integer of 2, V is carbon atom substituted with Zx, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (41) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁶ is carbon atom substituted with Zx, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (42) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁶ is carbon atom substituted with Zx, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (43) The compound or salt thereof according to any one of (39) to (42) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (44) The compound or salt thereof according to any one of (39) to (43) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (45) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁶ is carbon atom substituted with Zx, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

Zx is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl, group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(46) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, and C² and C⁶ are unsubstituted ring-constituting carbon atoms. (47) The compound or salt thereof according to (46) mentioned above, wherein, in the formula (I), n is an integer of 2, D is oxygen atom, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (48) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (49) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (50) The compound or salt thereof according to any one of (46) to (49) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (51) The compound or salt thereof according to any one of (46) to (50) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)- or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (52) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(53) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, and D is a single bond, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (53-2) The compound of salt thereof according to (1-2) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, and D is a single bond, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (53-3) The compound or salt thereof according to (53) or (53-2) mentioned above, wherein, in the formula (I), Rs is -D-Rx and D is single bond. (54) The compound or salt thereof according to any one of (53) to (53-3) mentioned above, wherein, in the formula (I), n is an integer of 2, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (55) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, D is a single bond, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (55-2) The compound or a salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, D is a single bond, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (56) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁶ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, D is a single bond, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (56-2) The compound or a salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, D is a single bond, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (57) The compound or salt thereof according to any one of (53) to (56-2) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (58) The compound or salt thereof according to any one of (53) to (57) mentioned above, wherein, in the formula (I), Rs is -D-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)- or —N(ethyl)-, A¹ represents ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (58-2) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms, V is nitrogen atom or V is carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is -D-Rx, D is a single bond, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rx is Rb or Rc (provided that Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group), A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² represents oxygen atom, sulfur atom, —N(methyl)- or —N(ethyl)-, A¹ represents ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group, (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(58-3) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms, V is nitrogen atom or V is carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is -D-Rx, D is a single bond, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, biphenyl-2-yl group, biphenyl 3-yl group, biphenyl-4-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(58-4) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom or V is carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is -D-Rx, D is a single bond, Rx is phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, or 1-methyl-1H-indazol-5-yl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(58-5) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E),

Rs binds to C⁴ in the aromatic ring (E), C², C⁵, and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rx, D is a single bond, Rx is phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, or 1-methyl-1H-indazol-5-yl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and Y is hydrogen atom, methyl group, or ethyl group.

(59) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is —S-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(59-2) The compound or salt thereof according to (1) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, and Rs is —N(Ry)(Rz). (59-3) The compound or salt thereof according to (1) mentioned above, wherein, in the formula (I), AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, and Rs is —N(Ry)(Rz). (60) The compound or salt thereof according to (59-2) or (59-3) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (61) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —N(Ry)(Rz), and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (61-2) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —N(Ry)(Rz), and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (62) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —N(Ry)(Rz), and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (62-2) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —N(Ry)(Rz), and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (63) The compound or salt thereof according to any one of (59-2) to (62-2) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (64) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3, C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C², C⁵, and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —N(Ry)(Rz), Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2 (2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they bind,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa),

Xa represents oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(65) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C², C⁵ and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —N(Ry)(Rz), Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, or morpholino group together with the nitrogen atom to which they bind,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group

(65-2) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C², C⁵ and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —N(Ry)(Rz), and the group represented by —N(Ry)(Rz) is N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group, N-isopropyl-N-methylamino group, N-ethyl-N-isopropylamino group, N-butylamino group, N-butyl-N-methylamino group, N-butyl-N-ethylamino group, N-isobutylamino group, N-isobutyl-N-methylamino group, N-ethyl-N-isobutylamino group, N-(2-ethylbutyl)amino group, N-(2-ethylbutyl)-N-methylamino group, N-cyclopentylamino group, N-cyclopentyl-N-methylamino group, N-cyclohexylamino group, N-cyclohexyl-N-methylamino group, N-cycloheptylamino group, N-(cyclopentylmethyl)amino group, N-(cyclopentylmethyl)-N-methylamino group, N-(cyclohexylmethyl)amino group, N-(cyclohexylmethyl)-N-methylamino group, N-(2-methylphenyl)amino group, N-(4-methylphenyl)amino group, N-(2-fluorophenyl)amino group, N-(3-fluorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(2-chlorophenyl)amino group, N-(3-chlorophenyl)amino group, N-(4-chlorophenyl)amino group, N-(indan-2-yl)amino group, N-(1-phenylethyl)amino group, N-[1-(2-fluorophenyl)ethyl]amino group, N-[1-(3-fluorophenyl)ethyl]amino group, N-[1-(4-fluorophenyl)ethyl]amino group, N-[1-(2-chlorophenyl)ethyl]amino group, N-[1-(3-chlorophenyl)ethyl]amino group, N-[1-(4-chlorophenyl)ethyl]amino group, N-(2-methylphenylmethyl)amino group, N-methyl-N-(2-methylphenylmethyl)amino group, N-(3-methylphenylmethyl)amino group, N-methyl-N-(3-methylphenylmethyl)amino group, N-(4-methylphenylmethyl)amino group, N-methyl-N-(4-methylphenylmethyl)amino group, N-(2-fluorophenylmethyl)amino group, N-(2-fluorophenylmethyl)-N-methylamino group, N-(3-fluorophenylmethyl)amino group, N-(3-fluorophenylmethyl)-N-methylamino group, N-(4-fluorophenylmethyl)amino group, N-(4-fluorophenylmethyl)-N-methylamino group, N-(2-chlorophenylmethyl)amino group, N-(2-chlorophenylmethyl)-N-methylamino group, N-(3-chlorophenylmethyl)amino group, N-(3-chlorophenylmethyl)-N-methylamino group, N-(4-chlorophenylmethyl)amino group, N-(4-chlorophenylmethyl)-N-methylamino group, N-(2,3-difluorophenylmethyl)amino group, N-(2,3-difluorophenylmethyl)-N-methylamino group, N-(2,4-difluorophenylmethyl)amino group, N-(2,4-difluorophenylmethyl)-N-methylamino group, N-(2,5-difluorophenylmethyl)amino group, N-(2,5-difluorophenylmethyl)-N-methylamino group, N-(3,4-difluorophenylmethyl)amino group, N-(3,4-difluorophenylmethyl)-N-methylamino group, N-(3,5-difluorophenylmethyl)amino group, N-(3,5-difluorophenylmethyl)-N-methylamino group, N-(2,3-dichlorophenylmethyl)amino group, N-(2,3-dichlorophenylmethyl)-N-methylamino group, N-(2,4-dichlorophenylmethyl)amino group, N-(2,4-dichlorophenylmethyl)-N-methylamino group, N-(2,5-dichlorophenylmethyl)amino group, N-(2,5-dichlorophenylmethyl)-N-methylamino group, N-(2,6-dichlorophenylmethyl)amino group, N-(2,6-dichlorophenylmethyl)-N-methylamino group, N-(3,4-dichlorophenylmethyl)amino group, N-(3,4-dichlorophenylmethyl)-N-methylamino group, N-(3,5-dichlorophenylmethyl)amino group, N-(3,5-dichlorophenylmethyl)-N-methylamino group, N-[2-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[2-(trifluoromethyl)phenylmethyl]amino group, N-[3-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[3-(trifluoromethyl)phenylmethyl]amino group, N-[4-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[4-(trifluoromethyl)phenylmethyl]amino group, 1-pyrrolidino group, 1-(4-methylpiperidino) group, 1-homopiperidino group, or 4-morpholino group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(65-3) The compound or salt thereof according to (1) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ is nitrogen atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

Rs is —N(Ry)(Rz), and the group represented by —N(Ry)(Rz) is N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group, N-isopropyl-N-methylamino group, N-ethyl-N-isopropylamino group, N-butylamino group, N-butyl-N-methylamino group, N-butyl-N-ethylamino group, N-isobutylamino group, N-isobutyl-N-methylamino group, N-ethyl-N-isobutylamino group, N-(2-ethylbutyl)amino group, N-(2-ethylbutyl)-N-methylamino group, N-cyclopentylamino group, N-cyclopentyl-N-methylamino group, N-cyclohexylamino group, N-cyclohexyl-N-methylamino group, N-cycloheptylamino group, N-(cyclopentylmethyl)amino group, N-(cyclopentylmethyl)-N-methylamino group, N-(cyclohexylmethyl)amino group, N-(cyclohexylmethyl)-N-methylamino group, N-(2-methylphenyl)amino group, N-(4-methylphenyl)amino group, N-(2-fluorophenyl)amino group, N-(3-fluorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(2-chlorophenyl)amino group, N-(3-chlorophenyl)amino group, N-(4-chlorophenyl)amino group, N-(indan-2-yl)amino group, N-(1-phenylethyl)amino group, N-[1-(2-fluorophenyl)ethyl]amino group, N-[1-(3-fluorophenyl)ethyl]amino group, N-[1-(4-fluorophenyl)ethyl]amino group, N-[1-(2-chlorophenyl)ethyl]amino group, N-[1-(3-chlorophenyl)ethyl]amino group, N-[1-(4-chlorophenyl)ethyl]amino group, N-(2-methylphenylmethyl)amino group, N-methyl-N-(2-methylphenylmethyl)amino group, N-(3-methylphenylmethyl)amino group, N-methyl-N-(3-methylphenylmethyl)amino group, N-(4-methylphenylmethyl)amino group, N-methyl-N-(4-methylphenylmethyl)amino group, N-(2-fluorophenylmethyl)amino group, N-(2-fluorophenylmethyl)-N-methylamino group, N-(3-fluorophenylmethyl)amino group, N-(3-fluorophenylmethyl)-N-methylamino group, N-(4-fluorophenylmethyl)amino group, N-(4-fluorophenylmethyl)-N-methylamino group, N-(2-chlorophenylmethyl)amino group, N-(2-chlorophenylmethyl)-N-methylamino group, N-(3-chlorophenylmethyl)amino group, N-(3-chlorophenylmethyl)-N-methylamino group, N-(4-chlorophenylmethyl)amino group, N-(4-chlorophenylmethyl)-N-methylamino group, N-(2,3-difluorophenylmethyl)amino group, N-(2,3-difluorophenylmethyl)-N-methylamino group, N-(2,4-difluorophenylmethyl)amino group, N-(2,4-difluorophenylmethyl)-N-methylamino group, N-(2,5-difluorophenylmethyl)amino group, N-(2,5-difluorophenylmethyl)-N-methylamino group, N-(3,4-difluorophenylmethyl)amino group, N-(3,4-difluorophenylmethyl)-N-methylamino group, N-(3,5-difluorophenylmethyl)amino group, N-(3,5-difluorophenylmethyl)-N-methylamino group, N-(2,3-dichlorophenylmethyl)amino group, N-(2,3-dichlorophenylmethyl)-N-methylamino group, N-(2,4-dichlorophenylmethyl)amino group, N-(2,4-dichlorophenylmethyl)-N-methylamino group, N-(2,5-dichlorophenylmethyl)amino group, N-(2,5-dichlorophenylmethyl)-N-methylamino group, N-(2,6-dichlorophenylmethyl)amino group, N-(2,6-dichlorophenylmethyl)-N-methylamino group, N-(3,4-dichlorophenylmethyl)amino group, N-(3,4-dichlorophenylmethyl)-N-methylamino group, N-(3,5-dichlorophenylmethyl)amino group, N-(3,5-dichlorophenylmethyl)-N-methylamino group, N-[2-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[2-(trifluoromethyl)phenylmethyl]amino group, N-[3-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[3-(trifluoromethyl)phenylmethyl]amino group, N-[4-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[4-(trifluoromethyl)phenylmethyl]amino group, 1-pyrrolidino group, 1-(4-methylpiperidino) group, 1-homopiperidino group, or 4-morpholino group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(66) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (67) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (68) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (69) The compound or salt thereof according to any one of (66) to (68) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (70) The compound or salt thereof according to any one of (66) to (69) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is a group selected from butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, and cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (71) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ is carbon atom substituted with Zx, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

Zx is N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(72) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is -D-Rc, D is oxygen atom or sulfur atom, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (73) The compound or salt thereof according to (4) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rc, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (74) The compound or salt thereof according to (5) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rc, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (75) The compound or salt thereof according to any one of (72) to (74) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (76) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is -D-Rc, D is oxygen atom or sulfur atom, p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(77) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 2,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is —O-Rc, p in Rc is an integer of 2, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, or 4-fluorophenylmethyl group, Re is isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, or morpholino group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(78) The compound or salt thereof according to (7) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, n is an integer of 2, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Y is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. (79) The compound or salt thereof according to (78) mentioned above, wherein, in the formula (I), Xa which may substitute on AR is methyl group, ethyl group, propyl group, hydroxyethyl group, carboxymethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, methylamino group, dimethylamino group, carboxyl group, carbamoyl group, acetyl group, methanesulfonyl group, sulfamoyl group, or N,N-dimethylsulfamoyl group. (80) The compound or salt thereof according to (78) or (79) mentioned above, wherein, in the formula (I), Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, or cyclohexylmethyl group, or Rb (provided that Q in Rb is phenyl group or indan-2-yl group), A¹ is a single bond, or methylene group substituted with methyl group or ethyl group or unsubstituted methylene group, or ethylene group substituted with methyl group or ethyl group or unsubstituted ethylene group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), and R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, or dimethylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom). (81) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3,

C³ is carbon atom to which AR binds, C⁴ is carbon atom to which Rs binds, C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom, or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is —O-Rx, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bond or unsubstituted methylene, and A² is a single bond, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

AR is cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(82) The compound or salt thereof according to (6) mentioned above, wherein, in the formula (I), Link is —(CH₂)_(n)—, AR binds to C³ in the aromatic ring (E), Rs binds to C⁴ in the aromatic ring (E), C⁵ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C² and C⁶ are unsubstituted ring-constituting carbon atoms, Rs is —O-Rx, and Rx is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra or Rb. (83) The compound or salt thereof according to (82) mentioned above, wherein, in the formula (I), Zx is fluorine atom, chlorine atom, nitro group, amino group, methyl group, or OR⁹. (84) The compound or salt thereof according to (1-2) mentioned above, wherein, in the formula (I), n is an integer of 1 to 3, AR binds to C³, Rs binds to one of the ring-constituting atoms C⁴, C⁵, and C⁶, a ring-constituting carbon atom to which Rs does not bind among C⁴, C⁵, and C⁶ may be replaced with V,

V is nitrogen atom or carbon atom substituted with Zx, Zx is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group,

Rs is -D-Rx or —N(Ry)(Rz), D is oxygen atom or sulfur atom, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bind, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bind or unsubstituted methylene, and A² is a single bind, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group or ethyloxycarbonylamino group, Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-e]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

(85) A medicament containing a compound represented by the aforementioned formula (I) or a pharmacologically acceptable salt thereof as an active ingredient. (86) An agent for suppressing production of a prostaglandin and/or leukotriene, which contains a compound represented by the aforementioned formula (I) or a pharmacologically acceptable salt thereof as an active ingredient. (87) The medicament according to (85) for prophylactic and/or therapeutic treatment of a disease caused by production of a prostaglandin and/or leukotriene. (88) The medicament according to (85) for prophylactic and/or therapeutic treatment of an inflammatory disease of a mammal. (89) The medicament according to (85) for prophylactic and/or therapeutic treatment of an autoimmune disease of a mammal. (90) The medicament according to (85) for prophylactic and/or therapeutic treatment of an allergic disease of a mammal. (91) The medicament according to (85) for defervescence and/or pain relief of a mammal. (92) A pharmaceutical composition for prophylactic and/or therapeutic treatment of a condition of living body of a mammal exhibiting an acute or chronic inflammatory reaction, which comprises a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (I) or a pharmacologically acceptable salt thereof and a pharmaceutically acceptable carrier. (93) A method for prophylactic and/or therapeutic treatment of a condition of living body of a mammal exhibiting an acute or chronic inflammatory reaction, which comprises administering a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (I) or a pharmacologically acceptable salt thereof to the mammal. (94) A compound represented by the following formula (II):

[In the formula, each of C²′, C³′, C⁴′, C⁵′, and C⁶′ in the aromatic ring (E′) represents a ring-constituting carbon atom, any one of them to which Rs′ and G does not bind may be replaced with V′,

V′ represents nitrogen atom, or carbon atom substituted with Zx′, Zx′ has the same meaning as Zx mentioned above, provided that when Zx contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx contains amino group, the amino group may be protected with Rp²,

Rs′ represents -D-Rx′ or —N(Ry′)(Rz′),

-D-Rx′ and —N(Ry′)(Rz′) have the same meanings as -D-Rx and —N(Ry)(Rz), respectively, provided that when -D-Rx or —N(Ry)(Rz) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, when -D-Rx or —N(Ry)(Rz) contains amino group, the amino group may be protected with Rp²,

G represents chlorine atom, bromine atom, iodine atom, mesylate group, triflate group, or an arenesulfonate group of which aromatic portion may be substituted with one of T¹ or two or more of the same or different T¹, and Y′ represents a lower alkyl group having 1 to 4 carbon atoms].

(95) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to the ring-constituting carbon atom C²′ or C³′ in the aromatic ring (E′). (96) The compound according to (94) or (95) mentioned above, wherein, in the formula (II), n is an integer of 2. (97) The compound according to any one of (94) to (96) mentioned above, wherein, in the formula (II), Rs′ is —O-Rx′. (98) The compound according to any one of (94) to (97) mentioned above, wherein, in the formula (II), Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is a single bind, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—, Rx′ is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra, Rb, or Rc, k in Ra is 0 or an integer of 1 to 3, R¹ is a saturated cyclic alkyl group having 3 to 7 carbon atoms or a condensed saturated cyclic alkyl group having 6 to 8 carbon atoms, R¹ may be substituted with one of lower alkyl group having 1 to 4 carbon atoms or two or more of the same or different lower alkyl groups having 1 to 4 carbon atoms, Q in Rb is phenyl group, thienyl group, furyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, 4H-chromenyl group, dihydrobenzodioxyl group, benzoisoxazolyl group, pyrrolopyridinyl group, pyrazolopyridinyl group, triazolopyridinyl group, thienopyridinyl group, thienopyrazolyl group, 1,3-dihydrobenzimidazole group, dihydro-3H-benzoxazole group, or dihydro-3H-benzothiazole group, which binds to A² at an arbitrary position on the ring, A¹ is a single bind or an alkylene (a) having 1 to 3 carbon atoms, the alkylene (a) may be substituted with a lower alkyl group having 1 to 4 carbon atoms or phenyl group, A² is a single bind, oxygen atom, sulfur atom, —S(O)—, S(O)₂—, or —N(R⁴)— (provided that when A² is oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)—, A¹ is ethylene or trimethylene), R² and R³ independently represent hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, —OR⁵, —N(R⁶)(R⁶′), —NHCOR⁷, —NHSO₂R⁸, or -A⁶-Qa, or they bind to each other to form methylenedioxy group, Qa may be substituted with one of T¹ or two or more of the same or different T¹, and is phenyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, or indazolyl group, which binds to A⁶ at an arbitrary position on the ring, R⁴ and R⁶ independently represent hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R⁵ and R⁷ independently represent hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qa, R⁸ represents a lower alkyl group having 1 to 4 carbon atoms, R⁶′ has the same meaning as R⁶, or binds to R⁶ to form a 3- to 6-membered ring of a cycloalkyl group or morpholino group together with the nitrogen atom to which they bind, p in Rc is an integer of 2 to 4, A⁴ is a single bind or methylene or ethylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or Qa, Re is an alkyl group having 1 to 8 carbon atoms, -A⁶-Qa, —(CH₂)_(i)R¹⁴, —OR²⁸, —SR²⁸, or —N(R²⁹)(R³⁰), i is an integer of 1 to 3, R¹⁴ is hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, carboxyl group, or an N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms, R²⁸ is an alkyl group having 1 to 8 carbon atoms or -A⁶-Qa, R²⁹ is an alkyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or -A⁶-Qa, R³⁰ represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or binds to R²⁹ to form a 3- to 6-membered ring of nitrogen-containing cycloalkyl group or morpholino group together with the nitrogen atom to which they bind, Rz′ has the same meaning as Rx′, or represents -A⁵-Re, Ry′ represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qp, or binds to Rz′ to form a saturated or unsaturated nitrogen-containing cyclic substituent having 3 to 7 atoms together with the nitrogen atom to which they bind, when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp². (99) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 1 to 3,

G binds to C³′, Rs′ binds to one of the ring-constituting carbon atoms C⁴′, C⁵′, and C⁶′, a ring-constituting carbon atom to which Rs′ does not bind among C⁴′, C⁵′, and C⁶′ may be replaced with V′,

V′ is nitrogen atom or carbon atom substituted with Zx′, Zx′ is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is oxygen atom or sulfur atom, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bind, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bind or unsubstituted methylene, and A² is a single bind, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group or ethyloxycarbonylamino group, Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they binds, provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp²,

G is chlorine atom, bromine atom, iodine atom, or triflate group, and

Y′ is methyl group or ethyl group.

(100) The compound according to any one of (94) to (96) mentioned above, wherein, in the formula (II), Rs′ is —N(Ry′)(Rz′). (101) The compound according to any one of (94) to (96) mentioned above, wherein, in the formula (II), Rs′ is D-Rx′, and D is sulfur atom, —S(O)—, —S(O)₂— or —C(O)—. (102) The compound according to (94) mentioned above, wherein, in the formula (II), G binds at the position of C²′ in the aromatic ring (E′), Rs′ binds to one of the ring-constituting carbon atoms C³′, C⁴′ and C⁵′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V′. (103) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 1 to 3,

G binds to C²′, Rs′ binds to one of the ring-constituting carbon atoms C⁴′, C⁵′, and C⁶′, a ring-constituting carbon atom to which Rs′ does not bind among C³′, C⁴′, and C⁵′ may be replaced with V′,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is oxygen atom or sulfur atom, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bind, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bind or unsubstituted methylene, and A² is a single bind, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group, Rz is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom, provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp²,

G is chlorine atom, bromine atom, iodine atom, or triflate group, and

Y′ is methyl group or ethyl group.

(104) The compound according to (102) or (103) mentioned above, wherein, in the formula (II), n is an integer of 2, Rs′ binds to C³′ in the aromatic ring (E′), Rs′ is —O-Rx′, and Y′ is methyl group or ethyl group. (105) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C²′ is a ring-constituting carbon atom to which G binds, C³′ is a ring-constituting carbon atom to which Rs′ binds, C⁴′ may be replaced with V′, C⁵′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(106) The compound according to (102) or (103) mentioned above, wherein, in the formula (II), n is an integer of 2, Rs′ binds at the position of C⁴′ in the aromatic ring (E′), Rs′ is —O-Rx′, and Y is methyl group or ethyl group. (107) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C²′ is a ring-constituting carbon atom to which G binds, C⁴′ is a ring-constituting carbon atom to which Rs′ binds, C⁵′ may be replaced with V′, C³′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(108) The compound according to (102) or (103) mentioned above, wherein, in the formula (II), n is an integer of 2, Rs′ binds at the position of C⁵′ in the aromatic ring (E′), Rs′ is —O-Rx′, and Y′ is methyl group or ethyl group. (109) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁵′ or C⁶′ in the aromatic ring (E′), and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V′. (110) The compound according to (109) mentioned above, wherein, in the formula (II), n is an integer of 2, Rs′ binds to C⁵′ in the aromatic ring (E′), and Rs′ is —O-Rx′. (111) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁵′ is carbon atom to which Rs′ binds, C²′, C⁴′, and C⁶′ are unsubstituted ring-constituting carbon atoms,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(112) The compound according to (109) mentioned above, wherein, in the formula (II), n is an integer of 2, Rs′ binds to C⁶′ in the aromatic ring (E′), and Rs′ is —O-Rx′. (113) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), and C⁶′ is V′. (114) The compound according to (113) mentioned above, wherein, in the formula (II), n is an integer of 2, V′ is carbon atom substituted with Zx′, and Rs′ is —O-Rx′. (115) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is a carbon atom to which Rs′ binds, C⁶′ is carbon atom substituted with Zx′, C²′ and C⁵′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(116) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is nitrogen atom, and C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms. (117) The compound according to (116) mentioned above, wherein, in the formula (II), n is an integer of 2, and Rs′ is —O-Rx′. (118) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ is nitrogen atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(119) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and D is a single bind, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (120) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is a carbon atom to which Rs′ binds, C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —S-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(121) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —N(Ry′)(Rz′). (122) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is a carbon atom to which Rs′ binds, C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —N(Ry′)(Rz′), Rz′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry′ is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, or morpholino group together with nitrogen atom to which they binds, provided that when —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp²,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(123) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2, G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with —N(Rn¹)(Rn²) group (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (124) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ is carbon atom substituted with Zx′, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(125) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and Rx′ has the same meaning as Rc, provided that when Rc contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Rc contains amino group, the amino group may be protected with Rp². (126) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2,

C³′ is carbon atom to which G binds, C⁴′ is a carbon atom to which Rs′ binds, C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ has the same meaning as Rc, provided that when Rc contains hydroxyl group, the hydroxyl group may be protected with Rp¹, p in Rc is an integer of 2, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, or 4-fluorophenylmethyl group, Re is isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, or morpholino group,

G is bromine atom or iodine atom, and

Y′ is methyl group or ethyl group.

(127) The compound according to (94) mentioned above, wherein, in the formula (II), G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is —O-Rx′, and Rx′ is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra or Rb. (128) The compound according to (94) mentioned above, wherein, in the formula (II), n is an integer of 2, G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with nitro group, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (129) A compound represented by the following formula (III):

[In the formula, C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) represent a ring-constituting carbon atom, any one of these atoms to which Rs′ and AR′ does not bind may be replaced with V′, and AR′ has the same meaning as that of AR, provided that when AR contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR contains amino group, the amino group may be protected with Rp².]. (130) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to the atom of C²′ or C³′ in the aromatic ring (E′). (131) The compound according to (129) or (130) mentioned above, wherein, in the formula (III), AR′ is a residue of naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, dihydro-2H-isoquinoline, cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole, dihydro-3H-benzoxazole, phthalazine, [1,8]naphthalidine, [1,5]naphthalidine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrazolo[4,3-b]pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[3,4-b]pyridine, [1,2,4]triazolo[4,3-a]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, 1H-thieno[3,2-c]pyrazole, benzo[d]isoxazole, benzo[c]isoxazole, indolizine, 1,3-dihydroindole, 1H-pyrazolo[3,4-d]thiazole, 2H-isoindole, [1,2,4]triazolo[1,6-a]pyrimidine, 1H-pyrazolo[3,4-b]pyrazine, 1H-imidazo[4,5-b]pyrazine, 7H-purine, or 4H-chromene (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa, when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp²). (132) The compound according to (129) or (130) mentioned above, wherein, in the formula (III), AR′ is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa, when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp²). (133) The compound according to (129) or (130) mentioned above, wherein, in the formula (III), AR′ is a residue of naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, or dihydro-2H-isoquinoline (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa, when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp²). (134) The compound according to (129) or (130) mentioned above, wherein, in the formula (III), AR′ is a residue of cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole, dihydro-3H-benzoxazole, phthalazine, [1,8]naphthalidine, [1,5]naphthalidine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrazolo[4,3-b]pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[3,4-b]pyridine, [1,2,4]triazolo[4,3-a]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, 1H-thieno[3,2-c]pyrazole, benzo[d]isoxazole, benzo[c]isoxazole, indolizine, 1,3-dihydroindole, 1H-pyrazolo[3,4-d]thiazole, 2H-isoindole, [1,2,4]triazolo[1,5-a]pyrimidine, 1H-pyrazolo[3,4-b]pyrazine, 1H-imidazo[4,5-b]pyrazine, 7H-purine, or 4H-chromene (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa, when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp²). (135) The compound according to any one of (129) to (134) mentioned above, wherein, in the formula (III), Rs′ is —O-Rx′. (136) The compound according to any one of (129) to (135) mentioned above, wherein, in the formula (III), Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is a single bind, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—, Rx′ is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra, Rb, or Rc, k in Ra is 0 or an integer of 1 to 3, R¹ is a saturated cyclic alkyl group having 3 to 7 carbon atoms or a condensed saturated cyclic alkyl group having 6 to 8 carbon atoms, R¹ may be substituted with one of lower alkyl group having 1 to 4 carbon atoms or two or more of the same or different lower alkyl groups having 1 to 4 carbon atoms, Q in Rb is phenyl group, thienyl group, furyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, 4H-chromenyl group, dihydrobenzodioxyl group, benzoisoxazolyl group, pyrrolopyridinyl group, pyrazolopyridinyl group, triazolopyridinyl group, thienopyridinyl group, thienopyrazolyl group, 1,3-dihydrobenzimidazole group, dihydro-3H-benzoxazole group, or dihydro-3H-benzothiazole group, which binds to A² at an arbitrary position on the ring, A¹ is a single bind or an alkylene (a) having 1 to 3 carbon atoms, the alkylene (a) may be substituted with a lower alkyl group having 1 to 4 carbon atoms or phenyl group may be substituted with, A² is a single bind, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)— (provided that when A² is oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)—, A¹ is ethylene or trimethylene), R² and R³ independently represent hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, —OR⁵, —N(R⁶)(R⁶′), —NHCOR⁷, —NHSO₂R⁸, or -A⁶-Qa, or they binds to each other to form methylenedioxy group, Qa is phenyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, or indazolyl group, which may be substituted with one of T¹ or two or more of the same or different T¹, and binds to A⁶ at an arbitrary position on the ring, R⁴ and R⁶ independently represent hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R⁵ and R⁷ independently represent hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qa, R⁸ is a lower alkyl group having 1 to 4 carbon atoms, R⁶′ has the same meaning as R⁶, or binds to R⁶ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing alkyl group or morpholino group, p in Rc is an integer of 2 to 4, A⁴ is a single bind or methylene or ethylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or Qa, Re is an alkyl group having 1 to 8 carbon atoms, -A⁶-Qa, —(CH₂)_(i)R¹⁴, —OR²⁸, —SR²⁸, or —N(R²⁹)(R³⁰), i is an integer of 1 to 3, R¹⁴ is hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, carboxyl group, or an N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms, R²⁸ is an alkyl group having 1 to 8 carbon atoms or -A⁶-Qa, R²⁹ is an alkyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or -A⁶-Qa, R³⁰ is hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or binds to R²⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing alkyl group or morpholino group, Rz′ has the same meaning as Rx′, or represents -A⁵-Re, Ry′ is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qp, or binds to Rz′ to form a saturated or unsaturated nitrogen-containing cyclic substituent having 3 to 7 atoms, when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp². (137) The compound according to any one of (129) to (136) mentioned above, wherein, in the formula (III), Rs′ is —N(Ry′)(Rz′). (138) The compound according to any one of (129) to (136) mentioned above, wherein, in the formula (III), Rs′ is -D-Rx′, D is sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (139) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds at the position of C²′ in the aromatic ring (E′), and Rs′ binds to one of the ring-constituting carbon atoms C³′, C⁴′, and C^(5′.) (140) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C²′, Rs′ binds to any one of the atoms C³′, C⁴′, and C⁵′, a ring-constituting carbon atom to which Rs′ does not bind among C³′, C⁴′, and C⁵′ may be replaced with V′,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is one kind of group selected from the group consisting of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is oxygen atom or sulfur atom, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bind, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bind or unsubstituted methylene, and A² is a single bind, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group, Rz′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry′ is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group or pyrazol-1-yl group together with the nitrogen atom, provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp²,

AR′ is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl, group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), and Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(141) The compound according to (139) or (140) mentioned above, wherein, in the formula (III), Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V′. (142) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds at the position of C²′ in the aromatic ring (E′), Rs′ binds to one of the ring-constituting carbon atoms C³′, C⁴′, and C⁵′, Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V. (143) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds at the position of C²′ in the aromatic ring (E′), Rs′ binds to one of the ring-constituting carbon atoms C³′, C⁴′, and C⁵′, Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V. (144) The compound according to any one of (139) to (143) mentioned above, wherein, in the formula (III), Rs′ binds to C^(3′.) (145) The compound according to (129) mentioned above, wherein, in the formula (III), C²′ is carbon atom to which AR′ binds, C³′ is carbon atom to which Rs′ binds, C⁴′ may be replaced with V′, C⁵′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(146) The compound according to (139) to (143) mentioned above, wherein, in the formula (III), Rs′ binds to C^(4′.) (147) The compound according to (129) mentioned above, wherein, in the formula (III), C²′ is carbon atom to which AR′ binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ may be replaced with V′, C³′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(148) The compound according to any one of (139) to (143) mentioned above, wherein, in the formula (III), Rs′ binds to C⁵′. (149) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to the atom C⁵′ or C⁶′ in the aromatic ring (E′). (150) The compound according to (149) mentioned above, wherein, in the formula (III), Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V. (151) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to the atom C⁵′ or C⁶′ in the aromatic ring (E′), Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V. (152) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to the atom C⁵′ or C⁶′ in the aromatic ring (E′), Rs′ is —O-Rx′, and all of C²′, C³′, C⁴′, C⁵′ and C⁶′ in the aromatic ring (E′) are not replaced with V. (153) The compound according to any one of (149) to (152) mentioned above, wherein, in the formula (III), Rs′ binds to C^(5′.) (154) The compound according to (129) mentioned above, wherein, in the formula (III), C³′ is carbon atom to which AR′ binds, C⁵′ is carbon atom to which Rs′ binds, C²′, C⁴′, and C⁶′ are unsubstituted ring-constituting carbon atoms,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(155) The compound according to any one of (149) to (152) mentioned above, wherein, in the formula (III), Rs′ binds to C^(6′.) (156) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), and C⁶′ is V′. (157) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁶′ is carbon atom substituted with Zx, C²′ and C⁵′ are unsubstituted carbon atoms, and Rs′ is —O-Rx′. (158) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁶′ is carbon atom substituted with Zx, C²′ and C⁵′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (159) The compound according to (129) mentioned above, wherein, in the formula (III), C³′ is carbon atom to which AR′ binds, C⁴′ is a carbon atom to which Rs′ binds, C⁶′ is carbon atom substituted with Zx′, C²′ and C⁵′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when Ar′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(160) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is nitrogen atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (161) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is nitrogen atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (162) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is nitrogen atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (163) The compound according to (129) mentioned above, wherein, in the formula (III), C³′ is carbon atom to which AR′ binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ is nitrogen atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(164) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, D is a single bind, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (165) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and D is a single bind, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (166) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and D is a single bind, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. (167) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —N(Ry′)(Rz′). (168) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —N(Ry′)(Rz′). (169) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —N(Ry′)(Rz′). (170) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (171) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (172) The compound according to (123) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with —N(Rn¹)(Rn²) (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (173) The compound according to (129) mentioned above, wherein, in the formula (III), C³′ is carbon atom to which AR′ binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ is carbon atom substituted with Zx′, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(174) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and Rx′ has the same meaning as Rc, provided that when Rc contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Rc contains amino group, the amino group may be protected with Rp². (175) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and Rx′ has the same meaning as Rc, provided that when Re contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Re contains amino group, the amino group may be protected with Rp². (176) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is -D-Rx′, and Rx′ has the same meaning as Re, provided that when Re contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Re contains amino group, the amino group may be protected with Rp². (177) The compound according to (129) mentioned above, wherein, in the formula (III), C³′ is carbon atom to which AR′ binds, C⁴′ is a carbon atom to which Rs′ binds, C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms,

Zx′ is fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is —O-Rx′, Rx′ has the same meaning as Re, provided that when Re contains hydroxyl group, the hydroxyl group may be protected with Rp¹, p in Re is an integer of 2, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, or 4-fluorophenylmethyl group, Re is isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, or morpholino group, and

AR′ is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6 (2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(178) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′, Rs′ binds to any one of the atoms C⁴′, C⁵′, and C⁶′, a ring-constituting carbon atom to which Rs′ does not bind among C⁴′, C⁵′, and C⁶′ may be replaced with V′,

V′ is nitrogen atom, or carbon atom substituted with Zx′, Zx′ is fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx′ contains amino group, the amino group may be protected with Rp²,

Rs′ is -D-Rx′ or —N(Ry′)(Rz′), D is oxygen atom or sulfur atom, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rb or Rc, Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group, A² is a single bind, oxygen atom, sulfur atom., —N(methyl)-, or —N(ethyl)-(provided that when A² is oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ is ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q is phenyl group, A¹ is a single bind or unsubstituted methylene, and A² is a single bind, one of R² and R³ is a substituent other than hydrogen atom), p in Rc is an integer of 2 or 3, A⁴ is a single bind or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group or ethyloxycarbonylamino group, Rz′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, or (morpholino-4-yl)carbonyl group, Ry′ is hydrogen atom, methyl group, ethyl group or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom, provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituent -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp²,

AR′ is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), and Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when AR′ contains amino group, the amino group may be protected with Rp².

(179) The compound according to (119) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (180) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and D is oxygen atom. (181) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (182) The compound according to (129) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with nitro group, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (183) The compound according to (131) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with nitro group, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (184) The compound according to (132) mentioned above, wherein, in the formula (III), AR′ binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with nitro group, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. (185) An agent for prophylactic and/or therapeutic treatment of fibrosis, which contains a type 4 PLA₂ inhibitor as an active ingredient. (186) An agent for prophylactic and/or therapeutic treatment of pulmonary fibrosis, which contains a type 4 PLA₂ inhibitor as an active ingredient. (187) The prophylactic and/or therapeutic agent according to (186), wherein the pulmonary fibrosis is drug-induced pulmonary fibrosis. (188) The prophylactic and/or therapeutic agent according to (187), wherein the drug-induced pulmonary fibrosis is a disease induced by one or more kinds of medicaments among methotrexate, sodium aurothiomalate, auranofin, D-penicillamine, bucillamine, actarit, salazosulfapyridine, cyclophosphamide, Taxol, etoposide, cisplatin, vincristine, vinblastine, irinotecan, gefitinib, and bleomycin. (189) The prophylactic and/or therapeutic agent according to (187), wherein the drug-induced pulmonary fibrosis is a disease induced by one or more kinds of medicaments among methotrexate and bleomycin. (190) The prophylactic and/or therapeutic agent according to (186), wherein the type 4 PLA₂ inhibitor is a compound represented by the formula (I) or a pharmacologically acceptable salt thereof. (191) The prophylactic and/or therapeutic agent according to (186), wherein the type 4 PLA₂ inhibitor is an inhibitor selected from the group consisting of 4-(1-benzhydryl-6-chloro-1H-indol-3-ylmethyl)-3-methoxybenzoic acid, 4-{4-[2-(2-[bis(4-chlorophenyl)methoxy]ethylsulfonyl)ethoxy]phenyl}-1,1,1-trifluoro-2-butanone, N-{1-[2-(2,4-difluorobenzoyl)benzoyl]-4-tritylsulfanylpyrrolidin-2-ylmethyl}-4-(2,4-dioxothiazolidin-5-ylidenemethyl)benzoic acid amide, 4-methyl-2-oxo-5-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazolidine-3-carbonxylic acid (6-methoxytetrahydropyran-2-yl)amide, 4-methyl-2-oxo-5-(4-methylphenyl)thiazolidine-3-carbonxylic acid (tetrahydropyran-2-yl)amide, 4-[3-(4-decyloxyphenyloxy)-2-oxopropyloxy]benzoic acid, and 1-{2-[4-(carboxymethyl)phenoxy]ethyl}-3-dodecanoylindole-2-carbonxylic acid.

The compound (I) of the present invention or a pharmaceutically acceptable salt thereof has an action of suppressing the production of both of prostaglandins and leukotrienes, and said compound has characteristic features that, when administered to a human or animal, the compound exerts superior prophylactic and/or therapeutic effect on diseases or pathological conditions in which a prostaglandin and/or leukotriene is involved, and the compound has extremely low toxicity. The compounds (II) and (III) of the present invention are synthetic intermediates useful for the production of the compound (I) of the present invention. Furthermore, it was confirmed that a type 4 PLA₂ inhibitor is useful as a prophylactic and/or therapeutic agent for fibrosis, in particular, pulmonary fibrosis, especially drug-induced pulmonary fibrosis, which was induced as a side effect of a medicament.

BEST MODE FOR CARRYING OUT THE INVENTION

In the present specification, carbon atom may sometimes be represented simply by “C”, hydrogen atom by “H”, oxygen atom by “O”, sulfur atom by “S”, and nitrogen atom by “N”.

Examples of Link in the aforementioned general formula (I) include a saturated straight hydrocarbon chain having 1 to 3 carbon atoms or an unsaturated straight hydrocarbon chain having 2 or 3 carbon atoms. In the present invention, the straight chain of the saturated straight hydrocarbon chain is preferably unsubstituted. The straight chain of the unsaturated straight hydrocarbon chain is also preferably unsubstituted. As the saturated straight hydrocarbon chain, —(CH₂)_(n)— is preferred. Symbol n is an integer of 1 to 3. When n is 1, 2 or 3, the desired action is most characteristically exhibited. Methylene where n is 1, ethylene where n is 2 and trimethylene where n is 3 are preferred, and ethylene where n is 2 is particularly preferred.

The unsaturated hydrocarbon chain having 2 or 3 carbon atoms means a hydrocarbon chain which contains an unsaturated bond as a double bond or a triple bond among the carbon-carbon bonds. As the unsaturated hydrocarbon chain, an unsaturated hydrocarbon chain containing a double bond is preferred. When the chain contains one or more double bonds, the number of the double bond may preferably one. Specific examples include ethenylene which has two carbon atoms and contains one double bond, as well as ethynylene which has two carbon atoms and contains one triple bond, propen-3-yl which has three carbon atoms and contains one double bond, and propyn-3-yl which has three carbon atoms and contains one triple bond.

C², C³, C⁴, C⁵ and C⁶ in the aromatic ring (E) in the formula (I) each represent a ring-constituting carbon atom. The ring-constituting carbon atoms form the aromatic ring (E), and accordingly, they are represented as C or CH. Among them, any one of ring-constituting carbon atoms to which Rs or Ar does not bind may be replaced with V. The aforementioned expression “to be replaced with” means that any one of the ring-constituting carbon atoms C², C³, C⁴, C⁵ and C⁶ is replaced with V, and thus V may sometimes be a ring-constituting component. Rs and AR each bind to any of the ring-constituting carbon atoms C², C³, C⁴, C⁵ or C⁶ in the aromatic ring (E), and this means that, for example, when AR binds to C², Rs binds to any of the ring-constituting carbon atoms C³, C⁴, C⁵ and C⁶, when AR binds to C³, Rs binds to any of the ring-constituting carbon atoms C², C⁴, C⁵ and C⁶, and when AR bind to C⁴, Rs binds to the ring-constituting carbon atom C² or C³. Preferred examples of these combinations of substitution positions include a compound wherein AR binds to C², and Rs binds to any of the atoms C³, C⁴, and C⁵, and particularly preferred examples include a compound wherein AR binds to C², and Rs binds to C³ or C⁴. Preferred examples also include a compound wherein AR binds to C³, and Rs binds to any of the atoms C⁴, C⁵, and C⁶, and particularly preferred examples also include a compound wherein AR binds to C³, and Rs binds to the atom C⁴ or C⁵. A still more preferred example is a compound wherein AR binds to C³, and Rs binds to C⁴.

One of the atoms C², C³, C⁴, C⁵ and C⁶ to which Rs and AR do not bind may be replaced with V. For example, when AR binds to C², and Rs binds to C³, one of the ring-constituting carbon atoms C⁴, C⁵, and C⁶ may be replaced with V. As another example, it is meant that when AR binds to C³, and Rs binds to C⁴, one of the atoms C², C⁵, and C⁶ may be replaced with V. Among them combinations and other combinations, preferred examples are a compound wherein AR binds to C², Rs binds to C³, and C⁴ is replaced with V; a compound wherein AR binds to C², Rs binds to C⁴, and C⁵ is replaced with V; a compound wherein AR binds to C², Rs binds to C⁵, and C⁴ is replaced with V; a compound wherein AR binds to C³, Rs binds to C⁴, and C⁵ is replaced with V; a compound wherein AR binds to C³, Rs binds to C⁴, and C⁵ is replaced with V; a compound wherein AR binds to C³, Rs binds to C⁵, and C⁴ is replaced with V; a compound wherein AR binds to C³, Rs binds to C⁶, and C⁵ is replaced with V, and the like. Furthermore, particularly preferred examples include a compound wherein AR binds to C³, Rs binds to C⁴, and C⁵ is replaced with V; and a compound wherein AR binds to C³, Rs binds to C⁴, and C⁶ is replaced with V, and an particularly preferred example is a compound wherein AR binds to C³, Rs binds to C⁴, and C⁵ is replaced with V.

V represents nitrogen atom, or carbon atom substituted with Zx. Namely, when V represent nitrogen atom, the aromatic ring (E) in the formula (I) represents a pyridine ring. When V represent carbon atom substituted with Zx, the aromatic ring (E) is a benzene ring having Zx. Both of the compounds are particularly preferred. Furthermore, a compound wherein AR binds to C³, Rs binds to C⁴, C⁵ is V replaced with V, and this V represents nitrogen atom is particularly preferred.

Zx is defined as a linear or branched saturated alkyl group having 1 to 4 carbon atoms, fluorine atom, chlorine atom, bromine atom, nitro group, —OR⁹, or —N(Rn¹)(Rn²). Among them, fluorine atom, chlorine atom, bromine atom, and nitro group are preferred examples, and fluorine atom is particularly preferred.

As for Zx, examples of the linear or branched saturated alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group and the like, and among them, methyl group is particularly preferred.

R⁹ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or -A⁶-Qp. Among them, hydrogen atom is a particularly preferred example. Preferred examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and methyl group is particularly preferred.

A⁶ in -A⁶-Qp represents a single bond or methylene, and Qp represents a phenyl group which may be substituted with one of T¹ or two or more of the same or different T¹. The substituent T¹ is a linear or branched saturated alkyl group having 1 to 4 carbon atoms, hydroxyl group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, nitro group, an alkoxy group having 1 to 4 carbon atoms, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Specific examples of -A⁶-Qp include phenyl group, methylphenyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group, dichlorobenzyl group, fluorobenzyl group, trifluoromethylbenzyl group, nitrobenzyl group, methoxyphenyl group, N-methylaminobenzyl group, N,N-dimethylaminobenzyl group, and the like.

Preferred examples of —OR⁹ include hydroxyl group, methoxy group, and the like, and hydroxyl group is particularly preferred.

Rn¹ represents hydrogen atom or a linear or branched saturated alkyl group having 1 to 4 carbon atoms, and hydrogen atom is particularly preferred. Examples of the linear or branched saturated alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, or t-butyl group, and the like. Among them, methyl group, ethyl group, propyl group, isopropyl group, and the like are preferred examples, and methyl group is particularly preferred.

Rn² has the same meaning as Rn¹, or represents a —COR²³ group or a —SO₂R²⁴ group, or binds to Rn¹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group.

R²³ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, —O-A⁶-Qp, or —N(R²⁵)(R²⁶). R²⁵ represents hydrogen atom, or a linear or branched saturated alkyl group having 1 to 4 carbon atoms, R²⁶ has the same meaning as R²⁵, or binds to R²⁵ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group. Examples of the compound wherein R²⁶ “binds to R²⁵ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to represent a saturated nitrogen-containing cycloalkyl group or morpholino group” include, for example, a compound wherein a cyclic aminoalkyl group containing nitrogen atom such as pyrrolidino group, piperazino group and morpholino group is formed.

Specific examples of —COR²³ include formyl group, acetyl group, t-butyloxycarbonyl group, phenyloxycarbonyl group, benzyloxycarbonyl group, carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, piperidine-1-carbonyl group, morpholine-4-carbonyl group, and the like, and preferred examples include formyl group, acetyl group, carbamoyl group, and the like. In the aforementioned formulas, as represented by A⁶ and Qp, for example, the same symbols may sometimes be used simultaneously at different positions. These symbols are used to mean the same class of groups of substituents. However, because each substituent is independently chosen from each other, the same symbols do not mean that an identical substituent should be necessarily chosen, and as a result, selection of the same or different kind of substituent is not prohibited.

R²⁴ represents a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Specific examples of —SO₂R²⁴ include mesyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, and the like, and preferred examples include mesyl group, N,N-dimethylsulfamoyl group, and the like.

Specific examples of —N(Rn¹)(Rn²) include amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, piperidino group, pyrrolidino group, morpholino group, formylamino group, acetylamino group, t-butyloxycarbonylamino group, phenyloxycarbonylamino group, benzyloxycarbonylamino group, carbamoylamino group, N-methylcarbamoylamino group, N,N-dimethylcarbamoylamino group, piperidine-1-carbonylamino group, morpholine-4-carbonylamino group, mesylamino group, sulfamoylamino group, N-methylsulfamoylamino group, N,N-dimethylsulfamoylamino group, and the like. Among them, preferred examples include amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, N,N-dimethylsulfamoylamino group, and the like, and amino group, N-methylamino group, and N,N-dimethylamino group are particularly preferred.

Therefore, preferred examples of Zx include fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, N,N-dimethylsulfamoylamino group, and the like, and particularly preferred examples include fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, N,N-dimethylamino group, and the like.

In the formula (I), Rs is defined to represent -D-Rx or —N(Ry)(Rz).

D is defined to represent a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —C(O)—. Among them, oxygen atom and sulfur atom are preferred, and oxygen atom is particularly preferred. Another preferred examples include the compounds wherein D represent a single bond.

Rx represents a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or represents Ra, Rb, or Rc mentioned above.

As for Rx, examples of the linear or branched saturated alkyl group having 3 to 8 carbon atoms include; for example, propyl group, isopropyl group, butyl group, isobutyl group, 1-methylpropyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, hexyl group, 4-methylpentyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, octyl group, and the like, and butyl group, isobutyl group, and 2-ethylbutyl group are particularly preferred.

As for Rx, R¹ of Ra is defined to be a saturated cyclic alkyl group having 3 to 7 carbon atoms substituted with a lower alkyl group having 1 to 4 carbon atoms or an unsubstituted saturated cyclic alkyl group having 3 to 7 carbon atoms, or a condensed saturated cyclic alkyl group having 6 to 8 carbon atoms substituted with a lower alkyl group having 1 to 4 carbon atoms or an unsubstituted condensed saturated cyclic alkyl group having 6 to 8 carbon atoms. As for R¹, examples of the saturated cyclic alkyl group having 3 to 7 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and the like, and cyclopentyl group, cyclohexyl group, and cycloheptyl group are particularly preferred. As for R¹, examples of the condensed saturated cyclic alkyl group having 6 to 8 carbon atoms group include bicyclo[2,2,1]heptyl group, bicyclo[2,2,2]octyl group, and the like.

Examples of the lower alkyl group having 1 to 4 carbon atoms substituting on R¹ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like. Examples of R¹ substituted with a lower alkyl group having 1 to 4 carbon atoms include methylcyclopentyl group, methylcyclohexyl group, methylbicyclo[2,2,1]heptyl group, and the like.

Symbol k is defined to be 0 or an integer of 1 to 3. A single bond where k is 0, methylene where k is 1, and ethylene where k is 2 are preferred, and a bond where k is 0, and methylene where k is 1 are particularly preferred.

Examples of Ra include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, 3-cyclohexylpropyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, 3,4-dimethylcyclopentyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 4-ethylcyclohexyl group, 4-methylcyclohexylmethyl group, bicyclo[2,2,1]heptane-2-methyl group, bicyclo[2,2,2]octane-2-methyl group, 3-methylbicyclo[2,2,1]heptane-2-methyl group, bicyclo[2,2,1]hept-1-ylmethyl group, bicyclo[2,2,2]oct-1-ylmethyl group, and the like. Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group are preferred, and cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group are particularly preferred.

As for Rx, A² in Rb is defined to be a single bond, oxygen atom, sulfur atom, —S(O)—, —S(O)₂—, or —N(R⁴)—. R⁴ is defined to be a lower alkyl group having 1 to 4 carbon atoms. Preferred examples are methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and methyl group and ethyl group are particularly preferred examples. Therefore, particularly preferred examples of A² include a single bond, oxygen atom, sulfur atom, —N(methyl)-, and —N(ethyl)-.

A¹ is defined to be a single bond or an alkylene (a) having 1 to 3 carbon atoms, i.e., methylene, ethylene or trimethylene. However, when A² represents oxygen atom, sulfur atom, —S(O)—, —S(O)₂— or —N(R⁴)—, A¹ is ethylene or trimethylene Further, the alkylene (a) may be substituted with a lower alkyl group having 1 to 4 carbon atoms or phenyl group. Examples of the lower alkyl group having 1 to 4 carbon atoms for the above compound include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and methyl group, and ethyl group are preferred examples. Specific examples of A¹ include methylene, methylmethylene, ethylmethylene, phenylmethylene, ethylene, methylethylene, dimethylethylene, ethylethylene, phenylethylene, trimethylene, methyltrimethylene, and the like. Among them, when A² represents a single bond, A¹ is most preferably a single bond, or methylene, methylmethylene, or ethylene. Further, when A² represents oxygen atom, sulfur atom, —S(O)—, —S(O)₂— or —N(R⁴)—, A¹ is most preferably ethylene.

Q in Rb is defined to be a residue of a partially unsaturated or completely unsaturated monocyclic or condensed bicyclic carbon ring or heterocyclic ring (q), and the heterocyclic ring (q) means a ring containing 1 to 4 the same or different ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom. The term “residue” means a monovalent group formed by eliminating hydrogen atom bonding to a ring-constituting atom. The residue of monocyclic carbon ring or heterocyclic ring is a partially unsaturated or completely unsaturated substituent having 5 to 7 atoms, and examples include, for example, phenyl group, thienyl group, furyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, and the like. Among them, phenyl group, thienyl group, furyl group, pyridyl group, and oxazolyl group are preferred examples, and phenyl group is particularly preferred.

The condensed bicyclic carbon ring or heterocyclic ring is a partially unsaturated or completely unsaturated ring having 8 to 11 atoms, and examples of residue thereof include, for example, naphthyl group, tetrahydronaphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, 4H-chromenyl group, dihydrobenzodioxyl group, benzoisoxazolyl group, pyrrolopyridinyl group, pyrazolopyridinyl group, triazolopyridinyl group, thienopyridinyl group, thienopyrazolyl group, 1,3-dihydrobenzimidazole group, dihydro-3H-benzoxazole group, dihydro-3H-benzothiazole group, and the like. Among them, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group are preferred examples, and indanyl group is one of particularly preferred examples.

Q binds to A² at an arbitrary position on the ring. Preferred examples of Q with indication of bonding position include phenyl group, 2- or 3-thienyl group, 2- or 3-furyl group, 2-, 3- or 4-pyridyl group, 2-, 4- or 5-oxazolyl group, 1- or 2-naphthyl group, 1-, 2-, 5- or 6-tetrahydronaphthyl group, indan-1-yl group, indan-2-yl group, indan-4-yl group, indan-5-yl group, 1-, 2-, 3-, 4-, 5-, 6-, or 7-indolyl group, 2-, 5- or 6-dihydrobenzodioxyl group, and the like. Among them, phenyl group, and indan-2-yl group are particularly preferred.

In Rb, R² and R³ are defined to be substituents of Q, and independently represent hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, —OR⁵, —N(R⁶)(R⁶′), —NHCOR⁷, —NHSO₂R⁸, or -A⁶-Qa, or bind to each other to represent methylenedioxy group.

Examples of the linear or branched saturated alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and methyl group is particularly preferred.

R⁶ in —N(R⁶)(R⁶′) represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms. R⁶′ has the same meaning as R⁶, or binds to R⁶ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group. Therefore, specific examples of —N(R⁶)(R⁶′) include amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, piperidino group, pyrrolidino group, morpholino group, and the like. N,N-Dimethylamino group, piperidino group, morpholino group, and the like are preferred examples, and N,N-dimethylamino group is a particularly preferred example.

R⁵ and R⁷ are defined to independently represent hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a -A⁶-Qa group. Examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and among them, methyl group is a preferred example.

A⁶ in -A⁶-Qa has the same meaning as that defined above. Qa is defined to be a partially unsaturated or completely unsaturated monocyclic or condensed bicyclic carbon ring or heterocyclic ring (qa), and the heterocyclic ring (qa) means a substituent containing 1 to 4 the same or different ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom. The monocyclic carbon ring or heterocyclic ring is a partially unsaturated or completely unsaturated ring having 5 to 7 atoms, and examples of residue thereof include, for example, phenyl group, thienyl group, furyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, and the like. The condensed bicyclic carbon ring or heterocyclic ring is a partially unsaturated or completely unsaturated ring having 8 to 11 atoms, and examples of residue thereof include, for example, naphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, and the like.

Qa binds to A⁶ at an arbitrary position on the ring. Further, Qa may be substituted with two or more of the same or different T¹. T¹ has the same meaning as defined above.

Specific examples of -A⁶-Qa include phenyl group, methylphenyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group, dichlorobenzyl group, fluorobenzyl group, trifluoromethylbenzyl group, nitrobenzyl group, methoxyphenyl group, N-methylaminobenzyl group, N,N-dimethylaminobenzyl group, furyl group, thienyl group, pyrrolyl group, pyridyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, naphthyl group, indanyl group, indenyl group, quinolyl group, isoquinolyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, and the like.

R⁸ each defined to be a lower alkyl group having 1 to 4 carbon atoms, and examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like.

Therefore, preferred examples of R² and R³ include hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, and methylsulfonylamino group, and hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, and dimethylamino group are particularly preferred. When Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, at least one of R² and R³ preferably represents a substituent other than hydrogen atom.

Particularly preferred examples of Rb include 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3 (trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, and the like.

Symbol p in Rc is defined to be an integer of 2 to 4. Ethylene where p is 2, and trimethylene where p is 3 are preferred, and ethylene where p is 2 is particularly preferred. A⁴ represents a single bond, or represents methylene or ethylene, and a single bond and methylene are particularly preferred. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—, and all of them are preferred. Rd represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or group Qa. Re represents an alkyl group having 1 to 8 carbon atoms, a -A⁶-Qa group, a —(CH₂)_(i)R¹⁴ group, a —OR²⁸ group, a —SR²⁸ group, or a —N(R²⁹)(R³⁰) group. The group Qa and -A⁶-Qa have the same meanings as defined above.

The alkyl group having 1 to 8 carbon atoms is a linear or branched saturated alkyl group or a linear or branched partially unsaturated alkyl group, or an alkyl group which may contain a cycloalkyl group having 3 to 7 carbon atoms, and examples include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, hexyl group, 4-methylpentyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, octyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, 3,4-dimethylcyclopentyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 4-ethylcyclohexyl group, 4-methylcyclohexylmethyl group, and the like.

Symbol i in —(CH₂)_(i)R¹⁴ represents an integer of 1 to 3, and R¹⁴ represents hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, carboxyl group, or an N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms. Examples of the alkoxy group having 1 to 4 carbon atoms include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutyloxy group, t-butyloxy group, and the like. Examples of the N,N-dialkylcarbamoyl group having 1 to 4 carbon atoms include N,N-dimethylcarbamoyl group, N,N-diethylcarbamoyl group, and the like.

R²⁸ in —OR²⁸ or —SR²⁸ represents an alkyl group having 1 to 8 carbon atoms, or -A⁶-Qa, and these have the same meanings as defined above.

R²⁹ in —N(R²⁹)(R³⁰) represents an alkyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or -A⁶-Qa. Among them, the alkyl group having 1 to 8 carbon atoms and -A⁶-Qa have the same meanings as those defined above. Examples of the alkoxycarbonyl group having 1 to 4 carbon atoms include methyloxycarbonyl group, ethyloxycarbonyl group, propyloxycarbonyl group, isopropyloxycarbonyl group, butyloxycarbonyl group, isobutyloxycarbonyl group, t-butyloxycarbonyl group, and the like. R³⁰ represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, or binds to R²⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group. The lower alkyl group having 1 to 4 carbon atoms has the same meaning as defined above. Examples of the compound where “R³⁰ binds to R²⁹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group” include, for example, a compound wherein a cyclic aminoalkyl group containing nitrogen atom such as pyrrolidino group, piperazino group, and morpholino group is formed.

Preferred examples of Rd include hydrogen atom as well as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorobenzyl group, 4-fluorobenzyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, and the like.

Particularly preferred examples of Rd include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, and the like.

Preferred examples of substituted -A⁴-Rd include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, isoamyl group, cyclopropyl group, cyclopropylmethyl group, 2-(cyclopropyl)ethyl group, cyclopentyl group, cyclopentylmethyl group, 2-(cyclopentyl)ethyl group, cyclohexyl group, cyclohexylmethyl group, 2-(cyclohexyl)ethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, 2-(4-chlorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, (pyridin-2-yl)methyl group, (pyridin-3-yl)methyl group, (pyridin-4-yl)methyl group, and the like.

Particularly preferred examples of substituted -A⁴-Rd include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, isoamyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, 2-(4-chlorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, and the like.

Preferred examples of Re include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, methylthioxo group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, ethyloxycarbonylamino group, and the like.

Particularly preferred examples of Re include isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, morpholino group, and the like.

Preferred examples of -A⁵-Re include acetyl group, thioacetyl group, methanesulfonyl group, propionyl group, ethylthiocarbonyl group, butyryl group, propylthiocarbonyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, phenylmethylcarbonyl group, 4-methylphenylmethylcarbonyl group, 4-chlorophenylmethylcarbonyl group, 4-fluorophenylmethylcarbonyl group, (pyridin-2-yl)carbonyl group, (pyridin-2-yl)thiocarbonyl group, (pyridin-3-yl)carbonyl group, (pyridin-4-yl)carbonyl group, (furan-2-yl)carbonyl group, (thiophen-2-yl)carbonyl group, methyloxycarbonyl group, methylsulfanylcarbonyl group, methyloxythiocarbonyl group, methyloxycarbonylaminocarbonyl group, carbamoyl group, N-methylcarbamoyl group, N-methylthiocarbamoyl group, N,N-dimethylcarbamoyl group, N,N-dimethylthiocarbamoyl group, N,N-dimethylsulfamoyl group, ethyloxycarbonyl group, ethyloxycarbonylaminocarbonyl group, N-ethylcarbamoyl group, N-ethylthiocarbamoyl group, N,N-diethylcarbamoyl group, N,N-diethylthiocarbamoyl group, N,N-diethylsulfamoyl group, propyloxycarbonyl group, N-propylcarbamoyl group, N-propylthiocarbamoyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, phenylmethyloxycarbonyl group, 4-methylphenylmethyloxycarbonyl group, 4-chlorophenylmethyloxycarbonyl group, 4-fluorophenylmethyloxycarbonyl group, N-(pyridin-2-yl)carbamoyl group, N-(pyridin-2-yl)thiocarbamoyl group, N-(pyridin-3-yl)carbamoyl group, N-(pyridin-3-yl)thiocarbamoyl group, N-(pyridin-4-yl)carbamoyl group, N-(pyridin-4-yl)thiocarbamoyl group, N-(furan-2-yl)carbamoyl group, N-(thiophen-2-yl)carbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, (morpholino-4-yl)carbonyl group, and the like.

Particularly preferred examples of -A⁵-Re include isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, (morpholino-4-yl)carbonyl group, and the like.

Specific examples of Rc include 2-(N-isobutyryl-N-methylamino)ethyl group, 2-(N-ethyl-N-isobutyrylamino)ethyl group, 2-(N-isobutyryl-N-propylamino)ethyl group, 2-(N-isobutyryl-N-isopropylamino)ethyl group, 2-(N-butyl-N-isobutyrylamino)ethyl group, 2-(N-isobutyl-N-isobutyrylamino)ethyl group, 2-(N-cyclopropyl-N-isobutyrylamino)ethyl group, 2-(N-cyclopentyl-N-isobutyrylamino)ethyl group, 2-(N-cyclopentylmethyl-N-isobutyrylamino)ethyl group, 2-(N-cyclohexyl-N-isobutyrylamino)ethyl group, 2-(N-cyclohexylmethyl-N-isobutyrylamino)ethyl group, 2-(N-isobutyryl-N-phenylamino)ethyl group, 2-[N-isobutyryl-N-(4-methylphenyl)amino]ethyl group, 2-[N-(4-chlorophenyl)-N-isobutyrylamino]ethyl group, 2-[N-(4-fluorophenyl)-N-isobutyrylamino]ethyl group, 2-(N-benzyl-N-isobutyrylamino)ethyl group, 2-[N-(4-chlorophenylmethyl)-N-isobutyrylamino]ethyl group, 2-[N-(4-fluorophenylmethyl)-N-isobutyrylamino]ethyl group, 2-[N-[2-(4-chlorophenyl)ethyl]-N-isobutyrylamino]ethyl group, 2-[N-[2-(4-fluorophenyl)ethyl]-N-isobutyrylamino]ethyl group, 2-(N-isobutylthiocarbonyl-N-methylamino)ethyl group, 2-(N-isobutylthiocarbonyl-N-isopropylamino)ethyl group, 2-(N-butyl-N-isobutylthiocarbonylamino)ethyl group, 2-(N-isobutyl-N-isobutylthiocarbonylamino)ethyl group, 2-(N-cyclopentyl-N-isobutylthiocarbonylamino)ethyl group, 2-(N-cyclopentylmethyl-N-isobutylthiocarbonylamino)ethyl group, 2-(N-isobutylthiocarbonyl-N-phenylamino)ethyl group, 2-(N-benzyl-N-isobutylthiocarbonylamino)ethyl group, 2-[N-(4-fluorophenylmethyl)-N-isobutylthiocarbonylamino]ethyl group, 2-(N-methyl-N-pivaloylamino)ethyl group, 2-(N-isopropyl-N-pivaloylamino)ethyl group, 2-(N-butyl-N-pivaloylamino)ethyl group, 2-(N-isobutyl-N-pivaloylamino)ethyl group, 2-(N-cyclohexyl-N-pivaloylamino)ethyl group, 2-(N-cyclohexylmethyl-N-pivaloylamino)ethyl group, 2-(N-phenyl-N-pivaloylamino)ethyl group, 2-(N-benzyl-N-pivaloylamino)ethyl group, 2-(N-cyclopentylcarbonyl-N-methylamino)ethyl group, 2-(N-butyl-N-cyclopentylcarbonylamino)ethyl group, 2-(N-cyclopentylcarbonyl-N-isobutylamino)ethyl group, 2-(N-cyclopentylcarbonyl-N-cyclopentylmethylamino)ethyl group, 2-(N-cyclopentylcarbonyl-N-phenylamino)ethyl group, 2-[N-cyclopentylcarbonyl-N-(4-fluorophenyl)amino]ethyl group, 2-(N-benzyl-N-cyclopentylcarbonylamino)ethyl group, 2-[N-cyclopentylcarbonyl-N-(4-fluorophenylmethyl)amino]ethyl group, 2-(N-methyl-N-phenylsulfonylamino)ethyl group, 2-(N-ethyl-N-phenylsulfonylamino)ethyl group, 2-(N-phenylsulfonyl-N-propylamino)ethyl group, 2-(N-isopropyl-N-phenylsulfonylamino)ethyl group, 2-(N-butyl-N-phenylsulfonylamino)ethyl group, 2-(N-isobutyl-N-phenylsulfonylamino)ethyl group, 2-(N-cyclopropyl-N-phenylsulfonylamino)ethyl group, 2-(N-cyclopentyl-N-phenylsulfonylamino)ethyl group, 2-(N-cyclopentylmethyl-N-phenylsulfonylamino)ethyl group, 2-(N-cyclohexyl-N-phenylsulfonylamino)ethyl group, 2-(N-cyclohexylmethyl-N-phenylsulfonylamino)ethyl group, 2-(N-phenyl-N-phenylsulfonylamino)ethyl group, 2-[N-(4-fluorophenyl)-N-phenylsulfonylamino]ethyl group, 2-(N-benzyl-N-phenylsulfonylamino)ethyl group, 2-[N—(N-butylcarbamoyl)-N-methylamino]ethyl group, 2-[N-butyl-N—(N-butylcarbamoyl)amino]ethyl group, 2-[N—(N-butylcarbamoyl)-N-isobutylamino]ethyl group, 2-[N—(N-butylcarbamoyl)-N-cyclopentylamino]ethyl group, 2-[N—(N-butylcarbamoyl)-N-cyclohexylmethylamino]ethyl group, 2-[N—(N-butylcarbamoyl)-N-phenylamino]ethyl group, 2-{N—(N-butylcarbamoyl)-N-(4-fluorophenyl)amino}ethyl group, 2-[N-benzyl-N—(N-butylcarbamoyl)amino]ethyl group, 2-{N—(N-butylcarbamoyl)-N-(4-fluorophenylmethyl)amino}ethyl group, 2-{N—(N-butylcarbamoyl)-N-[2-(4-fluorophenyl)ethyl]amino}ethyl group, 2-[N—(N-isopropylthiocarbamoyl)-N-methylamino]ethyl group, 2-[N-butyl-N—(N-isopropylthiocarbamoyl)amino]ethyl group, 2-[N-isobutyl-N—(N-isopropylthiocarbamoylamino]ethyl group, 2-[N-cyclopentyl-N—(N-isopropylthiocarbamoyl)amino]ethyl group, 2-[N-cyclohexylmethyl-N—(N-isopropylthiocarbamoyl)amino]ethyl group, 2-[N—(N-isopropylthiocarbamoyl)-N-phenylamino]ethyl group, 2-{N-(4-fluorophenyl)-N—(N-isopropylthiocarbamoyl)amino}ethyl group, 2-[N-benzyl-N—(N-isopropylthiocarbamoyl)amino]ethyl group, 2-(N-isobutyloxycarbonyl-N-methylamino)ethyl group, 2-(N-butyl-N-isobutyloxycarbonylamino)ethyl group, 2-(N-isobutyl-N-isobutyloxycarbonylamino)ethyl group, 2-(N-cyclopentyl-N-isobutyloxycarbonylamino)ethyl group, 2-(N-cyclohexylmethyl-N-isobutyloxycarbonylamino)ethyl group, 2-(N-isobutyloxycarbonyl-N-phenylamino)ethyl group, 2-[N-(4-fluorophenyl)-N-isobutyloxycarbonylamino]ethyl group, 2-(N-benzyl-N-isobutyloxycarbonylamino)ethyl group, 2-[N—(N-cyclopentylcarbamoyl)-N-methylamino]ethyl group, 2-[N-butyl-N—(N-cyclopentylcarbamoyl)amino]ethyl group, 2-[N—(N-cyclopentylcarbamoyl)-N-isobutylamino]ethyl group, 2-[N-cyclopentyl-N—(N-cyclopentylcarbamoyl)amino]ethyl group, 2-[N-cyclohexylmethyl-N—(N-cyclopentylcarbamoyl)amino]ethyl group, 2-[N—(N-cyclopentylcarbamoyl)-N-phenylamino]ethyl group, 2-[N-benzyl-N—(N-cyclopentylcarbamoyl)amino]ethyl group, 2-[N—(N-cyclohexylthiocarbamoyl)-N-methylamino]ethyl group, 2-[N-butyl-N—(N-cyclohexylthiocarbamoyl)amino]ethyl group, 2-[N—(N-cyclohexylthiocarbamoyl)-N-isobutylamino]ethyl group, 2-[N—(N-cyclohexylthiocarbamoyl)-N-cyclopentylamino]ethyl group, 2-[N-cyclohexylmethyl-N—(N-cyclohexylthiocarbamoyl)amino]ethyl group, 2-[N—(N-cyclohexylthiocarbamoyl)-N-phenylamino]ethyl group, 2-[N-benzyl-N—(N-cyclohexylthiocarbamoyl)amino]ethyl group, 2-(N-methyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-butyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-isobutyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-cyclopentyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-cyclohexylmethyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-phenyl-N-phenyloxycarbonylamino)ethyl group, 2-(N-benzyl-N-phenyloxycarbonylamino)ethyl group, 2-[N-methyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-butyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-isobutyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-cyclopentyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-cyclohexylmethyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-phenyl-N—(N-phenylcarbamoyl)amino]ethyl group, 2-[N-benzyl-N—(N-phenylcarbamoyl)amino]ethyl group, and the like.

When Rs in the formula (I) represents —N(Ry)(Rz), Rz is defined to have the same meaning as Rx, or Rz represents methyl group, ethyl group, or a -A⁵-Re group. -A⁵-Re has the same meaning as defined above.

Particularly preferred examples of Rz include butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, (morpholino-4-yl)carbonyl group, and the like.

Among the Rz, methyl group or ethyl group is particularly preferred when Ry is other than hydrogen atom.

Ry represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a -A⁶-Qp group, or binds to Rz to form a saturated or unsaturated nitrogen-containing cyclic substituent having 3 to 7 atoms together with nitrogen atom to which they bind. The alkyl group having 1 to 8 carbon atoms is a linear or branched saturated alkyl group, a linear or branched partially unsaturated alkyl group, or an alkyl group which may contain a cyclic alkyl group having 3 to 7 carbon atoms. Examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, hexyl group, 4-methylpentyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, octyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, 3,4-dimethylcyclopentyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 4-ethylcyclohexyl group, 4-methylcyclohexylmethyl group, and the like. -A⁶-Qp has the same meaning as defined above.

Particularly preferred examples of Ry include hydrogen atom, methyl group, ethyl group, isobutyl group, and the like.

Ry also binds to Rz to represents a saturated or unsaturated nitrogen-containing cyclic substituent having 3 to 7 atoms formed together with the nitrogen atom to which they bind. Specific examples thereof include cyclic substituents containing nitrogen atom such as 1-pyrrolidino group, 1-piperidino group, 1-homopiperidino group, 1-piperazino group, 4-morpholino group, pyrrol-1-yl group, imidazol-1-yl group, and pyrazol-1-yl group, and all of these are preferred.

The nitrogen-containing cyclic substituent may be substituted with one or two lower alkyl groups having 1 to 4 carbon atoms wherein the two alkyl groups may be the same or different. Examples of the lower alkyl having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, or t-butyl group.

Among the substituent —N(Ry)(Rz), particularly preferred examples include N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group, N-isopropyl-N-methylamino group, N-ethyl-N-isopropylamino group, N-butylamino group, N-butyl-N-methylamino group, N-butyl-N-ethylamino group, N-isobutylamino group, N-isobutyl-N-methylamino group, N-ethyl-N-isobutylamino group, N-(2-ethylbutyl)amino group, N-(2-ethylbutyl)-N-methylamino group, N-cyclopentylamino group, N-cyclopentyl-N-methylamino group, N-cyclohexylamino group, N-cyclohexyl-N-methylamino group, N-cycloheptylamino group, N-(cyclopentylmethyl)amino group, N-(cyclopentylmethyl)-N-methylamino group, N-(cyclohexylmethyl)amino group, N-(cyclohexylmethyl)-N-methylamino group, N-(2-methylphenyl)amino group, N-(4-methylphenyl)amino group, N-(2-fluorophenyl)amino group, N-(3-fluorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(2-chlorophenyl)amino group, N-(3-chlorophenyl)amino group, N-(4-chlorophenyl)amino group, N-(indan-2-yl)amino group, N-(1-phenylethyl)amino group, N-[1-(2-fluorophenyl)ethyl]amino group, N-[1-(3-fluorophenyl)ethyl]amino group, N-[1-(4-fluorophenyl)ethyl]amino group, N-[1-(2-chlorophenyl)ethyl]amino group, N-[1-(3-chlorophenyl)ethyl]amino group, N-[1-(4-chlorophenyl)ethyl]amino group, N-(2-methylphenylmethyl)amino group, N-methyl-N-(2-methylphenylmethyl)amino group, N-(3-methylphenylmethyl)amino group, N-methyl-N-(3-methylphenylmethyl)amino group, N-(4-methylphenylmethyl)amino group, N-methyl-N-(4-methylphenylmethyl)amino group, N-(2-fluorophenylmethyl)amino group, N-(2-fluorophenylmethyl)-N-methylamino group, N-(3-fluorophenylmethyl)amino group, N-(3-fluorophenylmethyl)-N-methylamino group, N-(4-fluorophenylmethyl)amino group, N-(4-fluorophenylmethyl)-N-methylamino group, N-(2-chlorophenylmethyl)amino group, N-(2-chlorophenylmethyl)-N-methylamino group, N-(3-chlorophenylmethyl)amino group, N-(3 chlorophenylmethyl)-N-methylamino group, N-(4-chlorophenylmethyl)amino group, N-(4-chlorophenylmethyl)-N-methylamino group, N-(2,3-difluorophenylmethyl)amino group, N-(2,3-difluorophenylmethyl)-N-methylamino group, N-(2,4-difluorophenylmethyl)amino group, N-(2,4-difluorophenylmethyl)-N-methylamino group, N-(2,5-difluorophenylmethyl)amino group, N-(2,5-difluorophenylmethyl)-N-methylamino group, N-(3,4-difluorophenylmethyl)amino group, N-(3,4-difluorophenylmethyl)-N-methylamino group, N-(3,5-difluorophenylmethyl)amino group, N-(3,5-difluorophenylmethyl)-N-methylamino group, N-(2,3-dichlorophenylmethyl)amino group, N-(2,3-dichlorophenylmethyl)-N-methylamino group, N-(2,4-dichlorophenylmethyl)amino group, N-(2,4-dichlorophenylmethyl)-N-methylamino group, N-(2,5-dichlorophenylmethyl)amino group, N-(2,5-dichlorophenylmethyl)-N-methylamino group, N-(2,6-dichlorophenylmethyl)amino group, N-(2,6-dichlorophenylmethyl)-N-methylamino group, N-(3,4-dichlorophenylmethyl)amino group, N-(3,4-dichlorophenylmethyl)-N-methylamino group, N-(3,5-dichlorophenylmethyl)amino group, N-(3,5-dichlorophenylmethyl)-N-methylamino group, N-[2-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[2-(trifluoromethyl)phenylmethyl]amino group, N-[3-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[3-(trifluoromethyl)phenylmethyl]amino group, N-[4-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[4-(trifluoromethyl)phenylmethyl]amino group, 1-pyrrolidino group, 1-(4-methylpiperidino) group, 1-homopiperidino group, and 4-morpholino group.

A most preferred example of Rs in the aforementioned general formula (I) include Rs which meets the conditions of: Rs is -D-Rx wherein D is a single bond and Rx represents Rb, and A¹ and A² in Rb are single bonds. Specific examples include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, or 1-methyl-1H-indazol-5-yl group.

AR in the formula (I) is defined to be a residue of a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or heterocyclic ring (ar). Further, AR may be substituted with one of Xa or two or more of the same or different Xa. The heterocyclic ring (ar) means a ring containing 1 to 4 the same or different ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom.

The “condensed bicyclic carbon ring or heterocyclic ring” means a partially unsaturated or completely unsaturated ring having 8 to 11 atoms. Preferred examples include a partially unsaturated or completely unsaturated ring consisting of 8 atoms formed by fusion of 5-membered heterocyclic rings containing 1 or 2 ring-constituting heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms, a partially unsaturated or completely unsaturated ring consisting of 9 atoms formed by fusion of a 5-membered heterocyclic ring containing 1 or 2 ring-constituting heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms and a 6-membered carbon ring or a 6-membered heterocyclic ring containing 1 or 2 ring-constituting heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms, and a partially unsaturated or completely unsaturated substituent consisting of 10 atoms formed by fusion of a 6-membered carbon ring or a 6-membered heterocyclic ring containing 1 or 2 ring-constituting heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms and a 6-membered carbon ring or 6-membered heterocyclic rings containing 1 or 2 ring-constituting heteroatoms selected from, the group consisting of nitrogen, oxygen, and sulfur atom. As the carbon ring constituting AR not containing a heteroatom, among the rings constituting AR, naphthalene ring is particularly preferred. Further, as the heterocyclic ring (ar) containing a heteroatom, among the rings constituting AR, those containing 1 or 2 ring-constituting heteroatoms are preferred.

As for AR in the formula (I), specific examples of preferred ring constituting AR include naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, dihydro-2H-isoquinoline, cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole, dihydro-3H-benzoxazole, phthalazine, [1,8]naphthalidine, [1,5]naphthalidine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrazolo[4,3-b]pyridine, 1H-pyrazolo[4,3-c]pyridine, 1H-pyrazolo[3,4-c]pyridine, 1H-pyrazolo[3,4-b]pyridine, [1,2,4]triazolo[4,3-a]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, 1H-thieno[3,2-c]pyrazole, benzo[d]isoxazole, benzo[c]isoxazole, indolizine, 1,3-dihydroindol, 1H-pyrazolo[3,4-d]thiazole, 2H-isoindol, [1,2,4]triazolo[1,5-a]pyrimidine, 1H-pyrazolo[3,4-b]pyrazine, 1H-imidazo[4,5-b]pyrazine, 7H-purine, 4H-chromene, and the like. Among them, naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline and dihydro-2H-isoquinoline constitute a particularly preferred group, and cinnoline, quinazoline, quinoxaline, 1H-benzimidazole, benzoxazole, 1H-pyrrolo[3,2-b]pyridine, benzo[1,2,5]thiadiazole, 1H-benzotriazole, 1,3-dihydropyrrolo[2,3-b]pyridine, 1,3-dihydrobenzimidazole and dihydro-3H-benzoxazole also constitute a particularly preferred group. Further, naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, quinoline, 1H-indazole and isoquinoline are particularly preferred.

AR binds to any of the ring-constituting carbon atoms C², C³, C⁴, C⁵, and C⁶ in the aromatic ring (E) in the aforementioned formula (I) at an arbitrary carbon atom in AR. Preferred examples of the ring constituting AR include, as indicated with substitution position in the aromatic ring (E), naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, 4H-chromen-5-yl group, and the like. Among them, naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, indol-5-yl group, indol-4-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, quinolin-6-yl group, quinolin-3-yl group, dihydro-1H-quinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, dihydro-2H-isoquinolin-6-yl group, cinnolin-6-yl group, benzoxazol-5-yl group, and the like constitute a particularly preferred group, and naphthalen-2-yl group, benzofuran-5-yl group, benzo[b]thiophen-5-yl group, indol-5-yl group, benzothiazol-6-yl group, quinolin-6-yl group, quinolin-3-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, cinnolin-6-yl group, benzoxazol-5-yl group and the like are particularly preferred.

Further, AR may be substituted with one of Xa or the same or different two or more of Xa. Examples of substitution position of Xa include a carbon atom of AR not bonding to the aromatic ring (E), and/or when nitrogen atom is present, that nitrogen atom.

The substituent Xa represents a linear or branched saturated alkyl group having 1 to 4 carbon atoms, a saturated cyclic alkyl group having 3 to 7 carbon atoms, oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, —(CH₂)_(i)R¹⁴, —OR¹⁰, —N(R¹¹)(R¹²), —SO₂R¹³, or —COR²⁷. However, when nitrogen atom is present in AR, Xa which may substitute on the nitrogen atom represents a linear or branched saturated alkyl group having 1 to 4 carbon atoms, a saturated cyclic alkyl group having 3 to 7 carbon atoms, or —(CH₂)_(i)R¹⁴.

Preferred examples of the substituent Xa are oxo group, thioxo group, fluorine atom, chlorine atom, and trifluoromethyl group.

Examples of the linear or branched saturated alkyl group having 1 to 4 carbon atoms as the substituent Xa include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and among them, methyl group, ethyl group, and propyl group are particularly preferred.

Further, examples of the saturated cyclic alkyl group having 3 to 7 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and the like.

—(CH₂)_(i)R¹⁴ has the same meaning as defined above. Preferred examples are 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, and N,N-dimethylcarbamoylmethyl group, and a particularly preferred example is 2-hydroxyethyl group.

R¹⁰ in —OR¹⁰ represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a —(CH₂)_(i)R¹⁴ group, and among them, hydrogen atom is a particularly preferred example. Examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like. Among them, methyl group is particularly preferred. —(CH₂)_(i)R¹⁴ has the same meaning as defined above. Therefore, preferred examples of —OR¹⁰ are hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, and the like, and hydroxyl group, methoxy group, and 2-hydroxyethyloxy group are particularly preferred.

R¹¹ in —N(R¹¹)(R¹²) represents hydrogen atom, or a lower alkyl group having 1 to 4 carbon atoms, and R¹² represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, —COR¹⁵, or —SO₂R¹⁶, or binds to R¹¹ to form a 3- to 6-membered ring together with the nitrogen atom to which they bind to form a saturated nitrogen-containing cycloalkyl group or morpholino group. R¹⁵ in —COR¹⁵ represents a lower alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, amino group, a mono- or dialkylamino group having 1 to 4 carbon atoms, or -A⁶-Qa. R¹⁶ in —SO₂R¹⁶ represents a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Specific examples of —N(R¹¹)(R¹²) include amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, piperidino group, pyrrolidino group, morpholino group, 2-hydroxyethylamino group, formylamino group, acetylamino group, benzoyl group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, carbamoylamino group, N-methylcarbamoylamino group, N,N-dimethylcarbamoylamino group, methylsulfonylamino group, sulfamoylamino group, N-methylsulfamoylamino group, N,N-dimethylsulfamoylamino group, and the like. Among them, preferred examples are amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, and the like, and amino group, N-methylamino group, N,N-dimethylamino group, and 2-hydroxyethylamino group are particularly preferred.

R¹³ in —SO₂R¹³ represents a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Preferred examples of —SO₂R¹³ include methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, and the like.

R²⁷ in —COR²⁷ represents hydrogen atom, hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, a lower alkyl group having 1 to 4 carbon atoms, amino group, or a mono- or dialkylamino group having 1 to 4 carbon atoms. Specific examples of —COR²⁷ include formyl group, carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, acetyl group, propionyl group, carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, and the like. Carboxyl group, acetyl group, carbamoyl group, N,N-dimethylcarbamoyl group, and the like are preferred examples, and carboxyl group is particularly preferred.

Preferred examples of the group Xa include oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, N,N-dimethylcarbamoyl group, and the like. Particularly preferred examples of the group Xa include oxo group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, amino group, N-methylamino group, N,N-dimethylamino group, 2-hydroxyethylamino group, carboxyl group, and the like. Preferred examples of the group Xa which may substitute on nitrogen atom include methyl group, ethyl group, propyl group, hydroxymethyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, and N,N-dimethylcarbamoylmethyl group. Among them, particularly preferred examples are methyl group, ethyl group, propyl group, and 2-hydroxyethyl group.

Preferred examples of AR substituted with the group Xa or unsubstituted AR include naphthalen-1-yl group, naphthalen-2-yl group, 6-fluoronaphthalen-2-yl group, 6-chloronaphthalen-2-yl group, 6-(trifluoromethyl)naphthalen-2-yl group, 5-hydroxynaphthalen-1-yl group, 5-hydroxynaphthalen-2-yl group, 6-hydroxynaphthalen-1-yl group, 6-hydroxynaphthalen-2-yl group, 7-hydroxynaphthalen-1-yl group, 7-hydroxynaphthalen-2-yl group, 5-methoxynaphthalen-1-yl group, 5-methoxynaphthalen-2-yl group, 6-methoxynaphthalen-1-yl group, 6-methoxynaphthalen-2-yl group, 7-methoxynaphthalen-1-yl group, 7-methoxynaphthalen-2-yl group, 5-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 7-(2-hydroxyethyloxy)naphthalen-2-yl group, 5-(carboxymethyloxy)naphthalen-2-yl group, 6-(carboxymethyloxy)naphthalen-2-yl group, 7-(carboxymethyloxy)naphthalen-2-yl group, 5-(N,N-dimethylcarbamoylmethyloxy)naphthalen-2-yl group, 6-(N,N-dimethylcarbamoylmethyloxy)naphthalen-2-yl group, 7-(N,N-dimethylcarbamoylmethyloxy)naphthalen-2-yl group, 5-aminonaphthalen-1-yl group, 5-aminonaphthalen-2-yl group, 6-aminonaphthalen-1-yl group, 6-aminonaphthalen-2-yl group, 7-aminonaphthalen-1-yl group, 7-aminonaphthalen-2-yl group, 5-(N-methylamino)naphthalen-1-yl group, 5-(N-methylamino)naphthalen-2-yl group, 6-(N-methylamino)naphthalen-1-yl group, 6-(N-methylamino)naphthalen-2-yl group, 7-(N-methylamino)naphthalen-1-yl group, 7-(N-methylamino)naphthalen-2-yl group, 5-(N,N-dimethylamino)naphthalen-1-yl group, 5-(N,N-dimethylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-1-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 7-(N,N-dimethylamino)naphthalen-1-yl group, 7-(N,N-dimethylamino)naphthalen-2-yl group, 5-(2-hydroxyethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, 7-(2-hydroxyethylamino)naphthalen-2-yl group, 5-acetylaminonaphthalen-2-yl group, 6-acetylaminonaphthalen-2-yl group, 6-(2-aminoacetylamino)naphthalen-2-yl group, 6-(2-hydroxyacetylamino)naphthalen-2-yl group, 7-(2-hydroxyacetylamino)naphthalen-2-yl group, 6-[(furan-2-carbonyl)amino]naphthalen-2-yl group, 7-[(furan-2-carbonyl)amino]naphthalen-2-yl group, 6-[(benzene-2-carbonyl)amino]naphthalen-2-yl group, 7-[(benzene-2-carbonyl)amino]naphthalen-2-yl group, 6-carbamoylaminonaphthalen-2-yl group, 6-methylsulfonylaminonaphthalen-2-yl group, 6-sulfamoylaminonaphthalen-2-yl group, 6-(N,N-dimethylsulfamoylamino)naphthalen-2-yl group, 6-methanesulfonylnaphthalen-2-yl group, 6-sulfamoylnaphthalen-2-yl group, 6-(N-methylsulfamoyl)naphthalen-2-yl group, 6-(N,N-dimethylsulfamoyl)naphthalen-2-yl group, 6-carboxynaphthalen-2-yl group, benzo[b]furan-4-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-4-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-4-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-4-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, 2-carboxybenzo[b]furan-4-yl group, 2-carboxybenzo[b]furan-5-yl group, 2-carboxy-3-methylbenzo[b]furan-4-yl group, 2-carboxy-3-methylbenzo[b]furan-5-yl group, 3-acetylbenzo[b]furan-4-yl group, 3-acetylbenzo[b]furan-5-yl group, 3-acetyl-2-methylbenzo[b]furan-4-yl group, 3-acetyl-2-methylbenzo[b]furan-5-yl group, 3-hydroxymethylbenzo[b]furan-4-yl group, 3-hydroxymethylbenzo[b]furan-5-yl group, 3-hydroxymethyl-2-methylbenzo[b]furan-4-yl group, 3-hydroxymethyl-2-methylbenzo[b]furan-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-4-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-4-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-4-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 2-carboxybenzo[b]thiophen-4-yl group, 2-carboxybenzo[b]thiophen-5-yl group, 2-carboxy-3-methylbenzo[b]thiophen-4-yl group, 2-carboxy-3-methylbenzo[b]thiophen-5-yl group, 3-acetylbenzo[b]thiophen-4-yl group, 3-acetylbenzo[b]thiophen-5-yl group, 3-acetyl-2-methylbenzo[b]thiophen-4-yl group, 3-acetyl-2-methylbenzo[b]thiophen-5-yl group, 3-hydroxymethylbenzo[b]thiophen-4-yl group, 3-hydroxymethylbenzo[b]thiophen-5-yl group, 3-hydroxymethyl-2-methylbenzo[b]thiophen-4-yl group, 3-hydroxymethyl-2-methylbenzo[b]thiophen-5-yl group, 1H-indol-4-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-4-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-4-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-4-yl group, 2,3-dimethyl-1H-indol-5-yl group, 2-carboxy-1H-indol-4-yl group, 2-carboxy-1H-indol-5-yl group, 2-carboxy-3-methyl-1H-indol-4-yl group, 2-carboxy-3-methyl-1H-indol-5-yl group, 3-acetyl-1H-indol-4-yl group, 3-acetyl-1H-indol-5-yl group, 3-acetyl-2-methyl-1H-indol-4-yl group, 3-acetyl-2-methyl-1H-indol-5-yl group, 3-hydroxymethyl-1H-indol-4-yl group, 3-hydroxymethyl-1H-indol-5-yl group, 3-hydroxymethyl-2-methyl-1H-indol-4-yl group, 3-hydroxymethyl-2-methyl-1H-indol-5-yl group, 1-methyl-1H-indol-4-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-4-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-4-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-4-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 2-carboxy-1-methyl-1H-indol-4-yl group, 2-carboxy-1-methyl-1H-indol-5-yl group, 2-carboxy-1,3-dimethyl-1H-indol-4-yl group, 2-carboxy-1,3-dimethyl-1H-indol-5-yl group, 3-acetyl-1-methyl-1H-indol-4-yl group, 3-acetyl-1-methyl-1H-indol-5-yl group, 3-acetyl-1,2-dimethyl-1H-indol-4-yl group, 3-acetyl-1,2-dimethyl-1H-indol-5-yl group, 3-hydroxymethyl-1-methyl-1H-indol-4-yl group, 3-hydroxymethyl-1-methyl-1H-indol-5-yl group, 3-hydroxymethyl-1,2-dimethyl-1H-indol-4-yl group, 3-hydroxymethyl-1,2-dimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-4-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-4-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-4-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-4-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 2-carboxy-1-ethyl-1H-indol-4-yl group, 2-carboxy-1-ethyl-1H-indol-5-yl group, 2-carboxy-1-ethyl-3-methyl-1H-indol-4-yl group, 2-carboxy-1-ethyl-3-methyl-1H-indol-5-yl group, 3-acetyl-1-ethyl-1H-indol-4-yl group, 3-acetyl-1-ethyl-1H-indol-5-yl group, 3-acetyl-1-ethyl-2-methyl-1H-indol-4-yl group, 3-acetyl-1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-hydroxymethyl-1H-indol-4-yl group, 1-ethyl-3-hydroxymethyl-1H-indol-5-yl group, 1-ethyl-3-hydroxymethyl-2-methyl-1H-indol-4-yl group, 1-ethyl-3-hydroxymethyl-2-methyl-1H-indol-5-yl group, 1-propyl-1H-indol-4-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-4-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-4-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-4-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 2-carboxy-1-propyl-1H-indol-4-yl group, 2-carboxy-1-propyl-1H-indol-5-yl group, 2-carboxy-3-methyl-1-propyl-1H-indol-4-yl group, 2-carboxy-3-methyl-1-propyl-1H-indol-5-yl group, 3-acetyl-1-propyl-1H-indol-4-yl group, 3-acetyl-1-propyl-1H-indol-5-yl group, 3-acetyl-2-methyl-1-propyl-1H-indol-4-yl group, 3-acetyl-2-methyl-1-propyl-1H-indol-5-yl group, 3-hydroxymethyl-1-propyl-1H-indol-4-yl group, 3-hydroxymethyl-1-propyl-1H-indol-5-yl group, 3-hydroxymethyl-2-methyl-1-propyl-1H-indol-4-yl group, 3-hydroxymethyl-2-methyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-4-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-4-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-4-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-4-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, 2-carboxy-1-(2-hydroxyethyl)-1H-indol-4-yl group, 2-carboxy-1-(2-hydroxyethyl)-1H-indol-5-yl group, 2-carboxy-1-(2-hydroxyethyl)-3-methyl-1H-indol-4-yl group, 2-carboxy-1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 3-acetyl-1-(2-hydroxyethyl)-1H-indol-4-yl group, 3-acetyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, 3-acetyl-1-(2-hydroxyethyl)-2-methyl-1H-indol-4-yl group, 3-acetyl-1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-hydroxymethyl-1H-indol-4-yl group, 1-(2-hydroxyethyl)-3-hydroxymethyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-hydroxymethyl-2-methyl-1H-indol-4-yl group, 1-(2-hydroxyethyl)-3-hydroxymethyl-2-methyl-1H-indol-5-yl group, 1-carboxymethyl-1H-indol-4-yl group, 1-carboxymethyl-1H-indol-5-yl group, 1-carboxymethyl-2-methyl-1H-indol-4-yl group, 1-carboxymethyl-2-methyl-1H-indol-5-yl group, 1-carboxymethyl-3-methyl-1H-indol-4-yl group, 1-carboxymethyl-3-methyl-1H-indol-5-yl group, 1-carboxymethyl-2,3-dimethyl-1H-indol-4-yl group, 1-carboxymethyl-2,3-dimethyl-1H-indol-5-yl group, 2-carboxy-1-carboxymethyl-1H-indol-4-yl group, 2-carboxy-1-carboxymethyl-1H-indol-5-yl group, 2-carboxy-1-carboxymethyl-3-methyl-1H-indol-4-yl group, 2-carboxy-1-carboxymethyl-3-methyl-1H-indol-5-yl group, 3-acetyl-1-carboxymethyl-1H-indol-4-yl group, 3-acetyl-1-carboxymethyl-1H-indol-5-yl group, 3-acetyl-1-carboxymethyl-2-methyl-1H-indol-4-yl group, 3-acetyl-1-carboxymethyl-2-methyl-1H-indol-5-yl group, 1-carboxymethyl-3-hydroxymethyl-1H-indol-4-yl group, 1-carboxymethyl-3-hydroxymethyl-1H-indol-5-yl group, 1-carboxymethyl-3-hydroxymethyl-2-methyl-1H-indol-4-yl group, 1-carboxymethyl-3-hydroxymethyl-2-methyl-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-(N-methylamino)benzothiazol-6-yl group, 2-(N,N-dimethylamino)benzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, 2-methylquinolin-3-yl group, quinolin-6-yl group, 2-methylquinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 3-methylbenzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 3-methyl-1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1,3-dimethyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-ethyl-3-methyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 3-methyl-1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indazol-5-yl group, 1-(carboxymethyl)-1H-indazol-5-yl group, 1-(carboxymethyl)-3-methyl-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, benzo[c]isothiazol-5-yl group, 3-methylbenzo[c]isothiazol-5-yl group, 2-methyl-2H-indazol-5-yl group, 2,3-dimethyl-2H-indazol-5-yl group, 2-ethyl-2H-indazol-5-yl group, 2-ethyl-3-methyl-2H-indazol-5-yl group, 2-propyl-2H-indazol-5-yl group, 3-methyl-2-propyl-2H-indazol-5-yl group, 2-(2-hydroxyethyl)-2H-indazol-5-yl group, 2-(2-hydroxyethyl)-3-methyl-2H-indazol-5-yl group, 2-(carboxymethyl)-2H-indazol-5-yl group, 2-(carboxymethyl)-3-methyl-2H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 2-methyl-imidazo[1,2-a]pyridin-6-yl group, 3-methyl-imidazo[1,2-a]pyridin-6-yl group, 2,3-dimethyl-imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1,2,3-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 2-methyl-1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 3-methyl-1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 2,3-dimethyl-1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(carboxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(carboxymethyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(carboxymethyl)-3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(carboxymethyl)-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-methylisoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, 2-methylquinazolin-6-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 2-methylquinoxalin-6-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, 1-methyl-1H-benzimidazol-5-yl group, 2-methyl-1H-benzimidazol-5-yl group, 1,2-dimethyl-1H-benzimidazol-5-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 2-methylbenzoxazol-5-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, 1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[3,2-b]pyridin-5-yl group, 2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl group, 3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl group, 1,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-5-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1-methyl-1H-benzotriazol-5-yl group, 1-ethyl-1H-benzotriazol-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-2-on-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-2-on-4-yl group, 1-methyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-on-5-yl group, 1,3-dihydrobenzimidazol-2-on-5-yl group, 1,3-dihydrobenzimidazol-2-on-4-yl group, 1-methyl-1,3-dihydrobenzimidazol-2-on-5-yl group, 1,3-dihydrobenzimidazole-2-thion-5-yl group, 1,3-dihydrobenzimidazole-2-thion-4-yl group, 1-methyl-1,3-dihydrobenzimidazole-2-thion-5-yl group, 3H-benzoxazol-2-on-6-yl group, 3H-benzoxazol-2-on-7-yl group, 3H-benzoxazol-2-on-5-yl group, 3H-benzoxazol-2-on-4-yl group, 3-methyl-3H-benzoxazol-2-on-6-yl group, 3H-benzoxazole-2-thion-6-yl group, 3H-benzoxazole-2-thion-7-yl group, 3H-benzoxazole-2-thion-5-yl group, 3H-benzoxazole-2-thion-4-yl group, 3-methyl-3H-benzoxazole-2-thion-6-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl group, 1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl group, 2-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl group, 3-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl group, 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-c]pyridin-5-yl group, 2-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl group, 3-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl group, 1,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1-methyl-1H-pyrazolo[4,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrazolo[4,3-b]pyridin-5-yl group, 3-methyl-1H-pyrazolo[4,3-b]pyridin-5-yl group, 1,3-dimethyl-1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1-methyl-1H-pyrazolo[4,3-c]pyridin-6-yl group, 1-ethyl-1H-pyrazolo[4,3-c]pyridin-6-yl group, 3-methyl-1H-pyrazolo[4,3-c]pyridin-6-yl group, 1,3-dimethyl-1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl group, 1-ethyl-1H-pyrazolo[3,4-c]pyridin-5-yl group, 3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl group, 1,3-dimethyl-1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, 1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl group, 1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl group, 3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl group, 1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, 3-methyl[1,2,4]triazolo[4,3-a]pyridin-6-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, 2-methylthieno[3,2-c]pyridin-2-yl group, 3-methylthieno[3,2-c]pyridin-2-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 2-methylthieno[3,2-b]pyridin-2-yl group, 3-methylthieno[3,2-b]pyridin-2-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, 1-methyl-1H-thieno[3,2-c]pyrazol-5-yl group, 1-ethyl-1H-thieno[3,2-c]pyrazol-5-yl group, 3-methyl-1H-thieno[3,2-c]pyrazol-5-yl group, 1,3-dimethyl-1H-thieno[3,2-c]pyrazol-5-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, 3-methylbenzo[d]isoxazol-5-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, 3-methylbenzo[c]isoxazol-5-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-2-on-5-yl group, 1,3-dihydroindol-2-on-4-yl group, 1,3-dihydroindol-2-on-6-yl group, 1-methyl-1,3-dihydro-indol-2-on-5-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, 2-methyl-2H-isoindol-5-yl group, 4H-chromen-6-yl group, 4H-chromen-5-yl group, chromen-4-on-7-yl group, chromen-4-on-6-yl group, and the like.

Particularly preferred examples include naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, benzoxazol-5-yl group, and the like.

Particularly preferred examples include naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, benzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, benzoxazol-5-yl group, and the like.

In the formula (I), the group Y is defined to be hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, —(CH₂)_(m)N(R¹⁸)(R¹⁹), or —C(R²⁰)₂OC(O)A³R²′, and among them, hydrogen atom is particularly preferred.

Examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like. Among them, methyl group, and ethyl group are particularly preferred.

Symbol m in —(CH₂)_(m)N(R¹⁸)(R¹⁹) is defined to be an integer of 2 or 3. R¹⁸ is the same as R¹⁹, or binds to R¹⁹ to represent a saturated nitrogen-containing cycloalkyl group forming a 3- to 6-membered ring together with nitrogen atom, or form morpholino group together with nitrogen atom, and R¹⁹ is defined to be methyl group, ethyl group, or propyl group. Examples of —(CH₂)_(m)N(R¹⁸)(R¹⁹) include 2-(N,N-dimethylamino)ethyl group, 2-(N,N-diethylamino)ethyl group, 2-(N,N-dipropylamino)ethyl group, 3-(N,N-dimethylamino)propyl group, 3-(N,N-diethylamino)propyl group, 2-(N,N-dipropylamino)propyl group, 2-pyrrolidin-1-ylethyl group, 2-piperidin-1-ylethyl group, 2-morpholin-4-ylethyl group, 3-pyrrolidin-1-ylpropyl group, 3-piperidin-1-ylpropyl group, 3-morpholin-4-ylpropyl group, and the like.

R²⁰ in —C(R²⁰)₂OC(O)A³R²¹ is defined to be hydrogen atom, methyl group, ethyl group, or propyl group. R²¹ is defined to be a lower alkyl group having 1 to 4 carbon atoms, a cyclic saturated alkyl group having 3 to 6 carbon atoms group, or phenyl group. Examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like, and examples of the cyclic saturated alkyl group having 3 to 6 carbon atoms group include cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group. A³ is defined to be a single bond, or oxygen atom. Examples of —C(R²⁰)₂OC(O)A³R²¹ include acetoxymethyl group, propionyloxymethyl group, butyryloxymethyl group, (2-methylpropionyl)oxymethyl group, (2,2-dimethylpropionyl)oxymethyl group, cyclopropionyloxymethyl group, cyclopentanoyloxymethyl group, cyclohexanoyloxymethyl group, phenylcarboxymethyl group, 1-acetoxy-1-methylethyl group, 1-methyl-1-(2-methylpropionyloxy)ethyl group, 1-cyclopentanoyloxy-1-methylethyl group, 1-cyclohexanoyloxy-1-methylethyl group, methoxycarbonyloxymethyl group, ethoxycarbonyloxymethyl group, isopropyloxycarbonyloxymethyl group, t-butyloxycarbonyloxymethyl group, cyclopropyloxycarbonyloxymethyl group, cyclopentyloxycarbonyloxymethyl group, cyclohexyloxycarbonyloxymethyl group, phenyloxycarbonyloxymethyl group, 1-methoxycarbonyloxy-1-methylethyl group, 1-ethoxycarbonyloxy-1-methylethyl group, 1-isopropyloxycarbonyloxy-1-methylethyl group, 1-t-butyloxycarbonyloxy-1-methylethyl group, 1-cyclopropyloxycarbonyloxy-1-methylethyl group, 1-cyclopentyloxycarbonyloxy-1 methylethyl group, 1-cyclohexyloxycarbonyloxy-1-methylethyl group, 1-methyl-1-phenyloxycarbonyloxyethyl group, and the like.

In a preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

AR binds to C², Rs binds to any of the atoms C³, C⁴ and C⁵, and a ring-constituting carbon atom to which Rs does not bind among C³, C⁴, and C⁵ may be replaced with V.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents -D-Rx, or —N(Ry)(Rz). D represents oxygen atom, or sulfur atom. Rx represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl), or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group.

Rz represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with nitrogen atom.

AR represents naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol 5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

AR binds to C³, Rs binds to any of the atoms C⁴, C⁵, and C⁶, and a ring-constituting carbon atom to which Rs does not bind among C⁴, C⁵, and C⁶ may be replaced with V.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents -D-Rx, or —N(Ry)(Rz). D represents oxygen atom, or sulfur atom. Rx represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb, or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group. Rz represents a group as any of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they binds.

AR represents naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In a preferred embodiment of the present invention, a compound or a salt thereof satisfying all of the following requirements is excluded from the compound represented by the formula (I) or a salt thereof.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ represents a ring-constituting carbon atom which may be substituted with Zx, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

Zx represents fluorine atom, chlorine atom, nitro group, amino group, methyl group, or a OR⁹ group, and R⁹ represents hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms.

Rs represents —O-Rx. Rx represents a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or represents Ra or Rb, Q in Rb represents a residue of a partially unsaturated or completely unsaturated monocyclic or condensed bicyclic carbon ring or heterocyclic ring (q), and binds to A² at an arbitrary position on the ring. The heterocyclic ring (q) contains one or two of the same or different ring-constituting heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom.

AR represents a residue of naphthalene, benzofuran, benzo[b]thiophene, indole, benzothiazole, dihydro-3H-benzothiazole, quinoline, dihydro-1H-quinoline, benzo[d]isothiazole, 1H-indazole, benzo[c]isothiazole, 2H-indazole, imidazo[1,2-a]pyridine, 1H-pyrrolo[2,3-b]pyridine, isoquinoline, or dihydro-2H-isoquinoline (the aforementioned residue may be substituted with one of Xa or two or more of the same or different Xa).

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents —O-Rx. Rx represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group.

AR represents any one of cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, and 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents —S-Rx. Rx represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl), or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group.

AR represents naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, and C², C⁵ and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents —N(Ry)(Rz). Rz represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they bind.

AR represents naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 1 to 3.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents -D-Rc, and D represents oxygen atom or sulfur atom. Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group., cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group.

AR represents naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (these groups may be substituted with one of Xa or two or more of the same or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link is —(CH₂)_(n)—, n is an integer of 1 to 3, C³ is carbon atom bound with AR, C⁴ is carbon atom bound with R⁵, C⁵ may be replaced with V, C² and C⁶ are unsubstituted ring-constituting carbon atoms,

V is nitrogen atom or V is carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs is -D-Rx, D is a single bond, Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or Rx is Rb or Rc (provided that Q in Rb is phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, or dihydrobenzodioxyl group), A² is a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-(provided that when A² represents oxygen atom, sulfur atom, —N(methyl)- or —N(ethyl)-, A¹ represents ethylene), R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group, p in Rc is an integer of 2 or 3, A⁴ is a single bond or methylene, A⁵ is —C(O)—, —C(S)—, or —S(O)₂—, Rd is hydrogen atom, or methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, or pyridin-4-yl group, Re is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, or ethyloxycarbonylamino group,

AR is naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, or 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of the same or different Xa), Xa is oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, or N,N-dimethylcarbamoyl group, and

Y is hydrogen atom, methyl group, or ethyl group.

In a particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C² represents carbon atom to which AR bonds, C³ represents carbon atom to which Rs bonds, C⁴ may be replaced with V, and C⁵ and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n), symbol n represents an integer of 2.

C² represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C³ and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as, any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁵ represents carbon atom to which Rs bonds, and C², C⁴ and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ represents nitrogen atom, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁶ represents carbon atom substituted with Zx, and C² and C⁵ represent unsubstituted ring-constituting carbon atom.

Zx represents fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, and C², C⁵ and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents —N(Ry)(Rz). Rz represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, or morpholino group together with nitrogen atom to which they bonds.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, and C², C⁵ and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents —N(Ry)(Rz). —N(Ry)(Rz) is any one of N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group, N-isopropyl-N-methylamino group, N-ethyl-N-isopropylamino group, N-butylamino group, N-butyl-N-methylamino group, N-butyl-N-ethylamino group, N-isobutylamino group, N-isobutyl-N-methylamino group, N-ethyl-N-isobutylamino group, N-(2-ethylbutyl)amino group, N-(2-ethylbutyl)-N-methylamino group, N-cyclopentylamino group, N-cyclopentyl-N-methylamino group, N-cyclohexylamino group, N-cyclohexyl-N-methylamino group, N-cycloheptylamino group, N-(cyclopentylmethyl)amino group, N-(cyclopentylmethyl)-N-methylamino group, N-(cyclohexylmethyl)amino group, N-(cyclohexylmethyl)-N-methylamino group, N-(2-methylphenyl)amino group, N-(4-methylphenyl)amino group, N-(2-fluorophenyl)amino group, N-(3-fluorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(2-chlorophenyl)amino group, N-(3-chlorophenyl)amino group, N-(4-chlorophenyl)amino group, N-(indan-2-yl)amino group, N-(1-phenylethyl)amino group, N-[1-(2-fluorophenyl)ethyl]amino group, N-[1-(3-fluorophenyl)ethyl]amino group, N-[1-(4-fluorophenyl)ethyl]amino group, N-[1-(2-chlorophenyl)ethyl]amino group, N-[1-(3-chlorophenyl)ethyl]amino group, N-[1-(4-chlorophenyl)ethyl]amino group, N-(2-methylphenylmethyl)amino group, N-methyl-N-(2-methylphenylmethyl)amino group, N-(3-methylphenylmethyl)amino group, N-methyl-N-(3-methylphenylmethyl)amino group, N-(4-methylphenylmethyl)amino group, N-methyl-N-(4-methylphenylmethyl)amino group, N-(2-fluorophenylmethyl)amino group, N-(2-fluorophenylmethyl)-N-methylamino group, N-(3-fluorophenylmethyl)amino group, N-(3-fluorophenylmethyl)-N-methylamino group, N-(4-fluorophenylmethyl)amino group, N-(4-fluorophenylmethyl)-N-methylamino group, N-(2-chlorophenylmethyl)amino group, N-(2-chlorophenylmethyl)-N-methylamino group, N-(3-chlorophenylmethyl)amino group, N-(3-chlorophenylmethyl)-N-methylamino group, N-(4-chlorophenylmethyl)amino group, N-(4-chlorophenylmethyl)-N-methylamino group, N-(2,3-difluorophenylmethyl)amino group, N-(2,3-difluorophenylmethyl)-N-methylamino group, N-(2,4-difluorophenylmethyl)amino group, N-(2,4-difluorophenylmethyl)-N-methylamino group, N-(2,5-difluorophenylmethyl)amino group, N-(2,5-difluorophenylmethyl)-N-methylamino group, N-(3,4-difluorophenylmethyl)amino group, N-(3,4-difluorophenylmethyl)-N-methylamino group, N-(3,5-difluorophenylmethyl)amino group, N-(3,5-difluorophenylmethyl)-N-methylamino group, N-(2,3-dichlorophenylmethyl)amino group, N-(2,3-dichlorophenylmethyl)-N-methylamino group, N-(2,4-dichlorophenylmethyl)amino group, N-(2,4-dichlorophenylmethyl)-N-methylamino group, N-(2,5-dichlorophenylmethyl)amino group, N-(2,5-dichlorophenylmethyl)-N-methylamino group, N-(2,6-dichlorophenylmethyl)amino group, N-(2,6-dichlorophenylmethyl)-N-methylamino group, N-(3,4-dichlorophenylmethyl)amino group, N-(3,4-dichlorophenylmethyl)-N-methylamino group, N-(3,5-dichlorophenylmethyl)amino group, N-(3,5-dichlorophenylmethyl)-N-methylamino group, N-[2-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[2-(trifluoromethyl)phenylmethyl]amino group, N-[3-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[3-(trifluoromethyl)phenylmethyl]amino group, N-[4-(trifluoromethyl)phenylmethyl]amino group, N-methyl-N-[4-(trifluoromethyl)phenylmethyl]amino group, 1-pyrrolidino group, 1-(4-methylpiperidino) group, 1-homopiperidino group, or 4-morpholino group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ represents carbon atom substituted with Zx, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

Zx represents N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents —O-Rx. Rx represents a group as any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, and Zx represents a group as any one of chlorine atom, bromine atom, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group.

Rs represents —O-Rc. p in Rc represents an integer of 2, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, and 4-fluorophenylmethyl group. Re represents a group as any one of isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, and morpholino group.

AR represents a group as any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group.

The group Y represents hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs represents -D-Rx and D represents a single bond. Rx is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, biphenyl-2-yl group, biphenyl 3-yl group, biphenyl-4-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, C⁵ may be replaced with V, and C² and C⁶ represent unsubstituted ring-constituting carbon atom.

V represents nitrogen atom, or carbon atom substituted with Zx, Zx is any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, or N,N-dimethylamino group,

Rs represents -D-Rx and D represents a single bond. Rx is phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, or 1-methyl-1H-indazol-5-yl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

In another particularly preferred embodiment of the present invention, the compound represented by the formula (I) or a salt thereof satisfies all of the following requirements.

Link represents —(CH₂)_(n)—, symbol n represents an integer of 2.

C³ represents carbon atom to which AR bonds, C⁴ represents carbon atom to which Rs bonds, and C², C⁵, and C⁶ represent unsubstituted ring-constituting carbon atom.

Rs represents -D-Rx and D represents a single bond. Rx is phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 3,5-dimethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 4-(N,N-dimethylamino)phenyl group, indan-2-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, naphthalen-1-yl group, naphthalen-2-yl group, 1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1H-indazol-5-yl group, or 1-methyl-1H-indazol-5-yl group,

AR is naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, or benzoxazol-5-yl group, and

Y is hydrogen atom, methyl group, or ethyl group.

Compound (I) of the present invention may have one or more asymmetric carbons depending on types of substituents. For example, as for a compound wherein the group Rs contains one or more asymmetric carbons, two kinds of optical isomers exist when the number of asymmetric carbon is 1, and when the number of asymmetric carbons is 2, four kinds of optical isomers and two kinds of diastereomers exist. Pure stereoisomers including optical isomers and diastereoisomers, any mixtures thereof, racemates and the like of the stereoisomers fall within the scope of the present invention. Further, Compound (I) of the present invention may exist as geometrical isomers based on a cycloalkyl ring structure, and any geometrical isomers in pure forms, and any mixtures of the geometrical isomers also fall within the scope of the present invention. Mixtures such as racemates may sometimes be preferred from a viewpoint of easiness for manufacture.

As a salt of Compound (I) of the present invention, a pharmaceutically acceptable salt is preferred. It is meant that, when at least one of the conditions (1) to (3) is satisfied: (1) Y is hydrogen atom; (2) the group AR contains carboxyl group or phenolic hydroxyl group; (3) the group Zx is phenolic hydroxyl group, and the like, then the compound forms 1 to 3 alkali salts depending on the number of acidic groups. Examples the alkali salts include, for example, salts with inorganic bases such as sodium and ammonia and salts with organic bases such as triethylamine.

Alternatively, it is meant that, when at least one of the conditions (1) to (4) is satisfied: (1) the group Rs has properties as a base as in a compound wherein Rs contains a substituted or unsubstituted amino group and the like; (2) AR itself is a cyclic substituent having properties as a base; (3) the group Ar contains a substituted or unsubstituted amino group; (4) any carbon atom in the aromatic ring (E) is replaced with V, and V is nitrogen atom, V is carbon atom substituted with Zx, and Zx is a substituted or unsubstituted amino group and the like, then the compound forms 1 to 4 acidic salts depending on the number of basic groups. Examples of the acidic salts include, for example, salts with inorganic acids such as hydrochloric acid and sulfuric acid and salts with organic acids such as acetic acid and citric acid.

C²′, C³′, C⁴′, C⁵′, and C⁶′ in the aromatic ring (E′) in the aforementioned formula (II) each represent a ring-constituting carbon atom. Among them, any ring-constituting carbon atom to which Rs′ and G do not bind may be replaced with V′. The substitution positions of Rs′, G, and V′ are similar to those described in the explanations of the substitution positions of Rs (corresponding to the position of Rs′), AR (corresponding to the position of the group G), and V (corresponding to the position of V′) in the aforementioned formula (I).

V′ represents nitrogen atom, or represents carbon atom substituted with Zx′. Zx′ has the same meaning as that of Zx, provided that when Zx contains hydroxyl group (OH), the hydroxyl group may be protected with Rp¹, and when Zx contains amino group (NH), the amino group may be protected with Rp².

Rs′ represents -D-Rx′ or —N(Ry′)(Rz′). -D-Rx′ and —N(Ry′)(Rz′) have the same meanings as those of -D-Rx and —N(Ry)(Rz) mentioned above, respectively. Provided that when -D-Rx and —N(Ry)(Rz) contain hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx and —N(Ry)(Rz) contains amino group (NH), the amino group may be protected with Rp².

Rp¹ represents, for example, a silyl group substituted with 3 of identical or different linear or branched saturated alkyl groups having 1 to 4 carbon atoms or phenyl groups, tetrahydropyranyl group, tetrahydrofuryl group, allyl group, propargyl group, benzyl group which may be substituted with one T¹ or two or more identical or different T¹, —CH₂—U-Rp³, —C(O)Rp³, —C(O)ORp³, or the like. U represents oxygen atom, or sulfur atom, and Rp³ represents hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms, trimethylsilylethyl group, chloromethyl group, trichloromethyl group, trifluoromethyl group, 9-fluorenylmethyl group, adamantyl group, allyl group, -A⁶-Qp, or the like. Rp² represents, for example, benzyl group which may be substituted with one of T¹ or two or more of identical or different T¹, —C(O)Rp³, —C(O)ORp³, or the like. However, the protective groups of hydroxyl group and amino group are not limited to these, and they can be chosen by referring and examining methods for introduction of protective groups and deprotection described in usual publications in the chemical field, for example, Protective Groups In Organic Synthesis, THIRD EDITION, published by John Wiley & Sons or the references cited therein.

G represents chlorine atom, bromine atom, iodine atom, mesylate group, triflate group, or an arenesulfonate group of which aromatic moiety may be substituted with one of T¹ or two or more identical or different T¹. Examples of the arenesulfonate group include, for example, benzenesulfonate group, p-toluenesulfonate group, mesitylenesulfonate group, 2,4,6-triisopropylbenzenesulfonate group, 4-fluorobenzenesulfonate group, 2,5-dichlorobenzenesulfonate group, 3-(trifluoromethyl)benzenesulfonate group, pentafluorobenzenesulfonate group, 2-nitrobenzenesulfonate group, 2,4-dinitrobenzenesulfonate group, and the like. Preferred examples of G include chlorine atom, bromine atom, iodine atom, triflate group, and the like, and bromine atom and iodine atom are particularly preferred examples.

Y′ represents a lower alkyl group having 1 to 4 carbon atoms. Examples of the lower alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, and the like. Among these, methyl group, and ethyl group are particularly preferred examples.

In the aforementioned formula (II), n and D have the same meaning as defined above.

In a preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 1 to 3.

The group G binds to C²′, Rs′ binds to any of the atoms C³′, C⁴′ and C⁵′, and a ring-constituting carbon atom to which Rs′ does not bind among C³′, C⁴′, and C⁵′ may be substituted with V′.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents -D-Rx′ or —N(Ry′)(Rz′). D represents oxygen atom or sulfur atom. Rx′ represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group. Rz′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry′ represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they bonds. Provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group (OH), the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp².

The group G represents chlorine atom, bromine atom, iodine atom, or triflate group.

The group Y′ represents methyl group, or ethyl group.

In another preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 1 to 3.

The group G binds to C³′, Rs′ binds to any of the atoms C⁴′, C⁵′, and C⁶′, and a ring-constituting carbon atom to which Rs′ does not bind among C⁴′, C⁵′ and C⁶′ may be replaced with V′.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents -D-Rx′, or —N(Ry′)(Rz′). D represents oxygen atom or sulfur atom. Rx′ represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group. Rz′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry′ represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with nitrogen atom. Provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp².

The group G represents chlorine atom, bromine atom, iodine atom, or triflate group.

The group Y′ represents methyl group, or ethyl group.

In a particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C²′ represents carbon atom to which the group G bonds, C³′ represents carbon atom to which Rs′ binds, C⁴′ may be replaced with V′, and C⁵′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C²′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ may be replaced with V′, and C³′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁵′ represents carbon atom to which Rs′ binds, and C²′, C⁴′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents nitrogen atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁶′ represents carbon atom substituted with Zx′, and

C²′ and C⁵′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁶′ represents carbon atom substituted with Zx′, or unsubstituted carbon atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —S-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents carbon atom substituted with Zx′, or unsubstituted ring-constituting carbon atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —N(Ry′)(Rz′). Rz′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry′ represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, or morpholino group together with the nitrogen atom to which they bonds. Provided that when —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Ry′ or Rz′ contains amino group, the amino group may be protected with Rp².

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents carbon atom substituted with Zx′, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group. Provided that when the substituted Zx′ contains amino group (NH), the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

In another particularly preferred embodiment, the compound represented by the formula (II) satisfies all of the following requirements.

Symbol n represents an integer of 2.

C³′ represents carbon atom to which the group G bonds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents carbon atom substituted with Zx′, or unsubstituted carbon atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ have the same meaning as that of Rc, provided that when Rc contains hydroxyl group (OH), the hydroxyl group may be protected with Rp¹. p in Rc represents an integer of 2, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, and 4-fluorophenylmethyl group. Re represents a group as any one of isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, and morpholino group.

The group G represents bromine atom, or iodine atom.

The group Y′ represents methyl group, or ethyl group.

C²′, C³′, C⁴′, C⁵′, and C⁶′ in the aromatic ring (E′) in the aforementioned formula (III) each represent a ring-constituting carbon atom. Any ring-constituting carbon atom to which Rs′ and AR′ do not bond among them may be replaced with V′. The substitution positions of Rs′, AR′, and V′ are similar to those described in the explanations of the substitution positions of Rs (corresponding to the position of Rs′), AR (corresponding to the position of the group AR′), and V (corresponding to the position of V′) in the aforementioned formula (I).

AR′ has the same meaning as that of AR mentioned above, provided that when AR contains hydroxyl group, the hydroxyl group may be protected with Rp¹. In this case, the hydroxyl group includes OH in carboxyl group (COOH). When the substituted AR contains amino group, the amino group represents a substituent, which may be protected with Rp². Examples of the amino group, which may be protected include NH present in a ring constituting AR, for example, as in indole ring, indazole ring, and the like.

Rs′, V, n, and D in the aforementioned formula (III) have the same meanings as those defined above. Rp¹, and Rp² also have the same meanings as those defined above.

In a preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

AR′ binds to C²′, Rs′ binds to any of the atoms C³′, C⁴′, and C⁵′, and a ring-constituting carbon atom to which Rs′ does not bind among C³′, C⁴′, and C⁶′ may be replaced with V′.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents -D-Rx′ or —N(Ry′)(Rz′). D represents oxygen atom or sulfur atom. Rx′ represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group. Rz′ represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry′ represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with the nitrogen atom to which they bond. However, -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp².

AR′ represents any one of naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, and 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of identical or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

AR′ binds to C³′, Rs′ binds to any of the ring-constituting carbon atoms C⁴′, C⁵′, and C⁶′, and a ring-constituting carbon atom to which Rs′ does not bind among C⁴′, C⁵′, and C⁶′ may be replaced with V′.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, chlorine atom, bromine atom, nitro group, methyl group, hydroxyl group, methoxy group, amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents -D-Rx′ or —N(Ry′)(Rz′). D represents oxygen atom or sulfur atom. Rx′ represents butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopentylethyl group, or 2-cyclohexylethyl group, or represents Rb or Rc. Q in Rb represents a group as any one of phenyl group, thienyl group, furyl group, pyridyl group, oxazolyl group, naphthyl group, tetrahydronaphthyl group, indanyl group, indolyl group, and dihydrobenzodioxyl group. A² represents a single bond, oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)- (provided that when A² represents oxygen atom, sulfur atom, —N(methyl)-, or —N(ethyl)-, A¹ represents ethylene). R² and R³ independently represent hydrogen atom, methyl group, fluorine atom, chlorine atom, trifluoromethyl group, methoxy group, dimethylamino group, acetylamino group, or methylsulfonylamino group (provided that when Q represents phenyl group, A¹ represents a single bond, or unsubstituted methylene, and A² represents a single bond, one of R² and R³ represents a substituent other than hydrogen atom). Symbol p in Rc represents an integer of 2 or 3, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents hydrogen atom, or a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopropylmethyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, and pyridin-4-yl group. Re represents any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, phenylmethyl group, 4-chlorophenylmethyl group, 4-fluorophenylmethyl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, thiomethoxy group, amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, N-(pyridin-2-yl)amino group, N-(pyridin-3-yl)amino group, N-(pyridin-4-yl)amino group, N-(furan-2-yl)amino group, N-(furan-3-yl)amino group, N-(thiophen-2-yl)amino group, N-(thiophen-3-yl)amino group, pyrrolidino group, piperidino group, morpholino group, methyloxycarbonylamino group, and ethyloxycarbonylamino group. Rz′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, 2-(N-ethyl-N-phenylamino)ethyl group, isobutyryl group, isopropylthiocarbonyl group, isopropylsulfonyl group, valeryl group, butylthiocarbonyl group, isovaleryl group, isobutylthiocarbonyl group, pivaloyl group, t-butylthiocarbonyl group, cyclopropylcarbonyl group, cyclopropylthiocarbonyl group, cyclopentylcarbonyl group, cyclopentylthiocarbonyl group, cyclohexylcarbonyl group, cyclohexylthiocarbonyl group, cyclopentylmethylcarbonyl group, cyclopentylmethylthiocarbonyl group, cyclohexylmethylcarbonyl group, cyclohexylmethylthiocarbonyl group, benzoyl group, thiobenzoyl group, phenylsulfonyl group, 4-methylphenylcarbonyl group, 4-methylphenylthiocarbonyl group, 4-methylphenylsulfonyl group, 4-chlorophenylcarbonyl group, 4-chlorophenylthiocarbonyl group, 4-fluorophenylcarbonyl group, 4-fluorophenylthiocarbonyl group, isopropyloxycarbonyl group, N-isopropylcarbamoyl group, N-isopropylthiocarbamoyl group, butyloxycarbonyl group, N-butylcarbamoyl group, N-butylthiocarbamoyl group, isobutyloxycarbonyl group, N-isobutylcarbamoyl group, N-isobutylthiocarbamoyl group, t-butyloxycarbonyl group, N-t-butylcarbamoyl group, N-t-butylthiocarbamoyl group, cyclopropyloxycarbonyl group, N-cyclopropylcarbamoyl group, N-cyclopropylthiocarbamoyl group, cyclopentyloxycarbonyl group, N-cyclopentylcarbamoyl group, N-cyclopentylthiocarbamoyl group, cyclohexyloxycarbonyl group, N-cyclohexylcarbamoyl group, N-cyclohexylthiocarbamoyl group, cyclopentylmethyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, phenyloxycarbonyl group, N-phenylcarbamoyl group, N-phenylthiocarbamoyl group, 4-methylphenyloxycarbonyl group, N-(4-methylphenyl)carbamoyl group, N-(4-methylphenyl)thiocarbamoyl group, 4-chlorophenyloxycarbonyl group, N-(4-chlorophenyl)carbamoyl group, N-(4-chlorophenyl)thiocarbamoyl group, 4-fluorophenyloxycarbonyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-fluorophenyl)thiocarbamoyl group, (pyrrolidino-1-yl)carbonyl group, (piperidino-1-yl)carbonyl group, and (morpholino-4-yl)carbonyl group. Ry′ represents hydrogen atom, methyl group, ethyl group, or isobutyl group, or binds to Rz′ to form pyrrolidino group, piperidino group, piperazino group, morpholino group, pyrrol-1-yl group, imidazol-1-yl group, or pyrazol-1-yl group together with nitrogen atom. Provided that when -D-Rx′ or —N(Ry′)(Rz′) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when -D-Rx′ or —N(Ry′)(Rz′) contains amino group, the amino group may be protected with Rp².

AR′ represents any one of naphthalen-2-yl group, naphthalen-1-yl group, benzofuran-5-yl group, benzofuran-4-yl group, benzofuran-2-yl group, benzo[b]thiophen-5-yl group, benzo[b]thiophen-4-yl group, benzo[b]thiophen-2-yl group, indol-5-yl group, indol-4-yl group, indol-6-yl group, benzothiazol-6-yl group, benzothiazol-7-yl group, benzothiazol-5-yl group, benzothiazol-4-yl group, dihydro-3H-benzothiazol-6-yl group, dihydro-3H-benzothiazol-7-yl group, dihydro-3H-benzothiazol-5-yl group, dihydro-3H-benzothiazol-4-yl group, quinolin-6-yl group, quinolin-3-yl group, quinolin-5-yl group, quinolin-7-yl group, dihydro-1H-quinolin-6-yl group, dihydro-1H-quinolin-5-yl group, benzo[d]isothiazol-5-yl group, benzo[d]isothiazol-4-yl group, benzo[d]isothiazol-6-yl group, benzo[d]isothiazol-7-yl group, 1H-indazol-5-yl group, 1H-indazol-4-yl group, 1H-indazol-6-yl group, benzo[c]isothiazol-5-yl group, benzo[c]isothiazol-4-yl group, benzo[c]isothiazol-6-yl group, benzo[c]isothiazol-7-yl group, 2H-indazol-5-yl group, 2H-indazol-4-yl group, 2H-indazol-6-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridin-7-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1H-pyrrolo[2,3-b]pyridin-4-yl group, isoquinolin-6-yl group, isoquinolin-3-yl group, isoquinolin-5-yl group, isoquinolin-7-yl group, dihydro-2H-isoquinolin-6-yl group, dihydro-2H-isoquinolin-5-yl group, cinnolin-6-yl group, cinnolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-5-yl group, quinoxalin-2-yl group, quinoxalin-6-yl group, quinoxalin-5-yl group, 1H-benzimidazol-5-yl group, 1H-benzimidazol-4-yl group, benzoxazol-5-yl group, benzoxazol-6-yl group, benzoxazol-4-yl group, benzoxazol-7-yl group, 1H-pyrrolo[3,2-b]pyridin-5-yl group, 1H-pyrrolo[3,2-b]pyridin-6-yl group, benzo[1,2,5]thiadiazol-5-yl group, benzo[1,2,5]thiadiazol-4-yl group, 1H-benzotriazol-5-yl group, 1H-benzotriazol-4-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-5-yl group, 1,3-dihydropyrrolo[2,3-b]pyridin-4-yl group, 1,3-dihydrobenzimidazol-5-yl group, 1,3-dihydrobenzimidazol-4-yl group, dihydro-3H-benzoxazol-6-yl group, dihydro-3H-benzoxazol-7-yl group, dihydro-3H-benzoxazol-5-yl group, dihydro-3H-benzoxazol-4-yl group, phthalazin-6-yl group, phthalazin-5-yl group, [1,8]naphthalidin-3-yl group, [1,8]naphthalidin-4-yl group, [1,5]naphthalidin-3-yl group, [1,5]naphthalidin-4-yl group, 1H-pyrrolo[3,2-c]pyridin-6-yl group, 1H-pyrrolo[3,2-c]pyridin-4-yl group, 1H-pyrrolo[2,3-c]pyridin-5-yl group, 1H-pyrrolo[2,3-c]pyridin-4-yl group, 1H-pyrazolo[4,3-b]pyridin-5-yl group, 1H-pyrazolo[4,3-b]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-6-yl group, 1H-pyrazolo[4,3-c]pyridin-4-yl group, 1H-pyrazolo[3,4-c]pyridin-5-yl group, 1H-pyrazolo[3,4-c]pyridin-4-yl group, 1H-pyrazolo[3,4-b]pyridin-5-yl group, 1H-pyrazolo[3,4-b]pyridin-4-yl group, [1,2,4]triazolo[4,3-a]pyridin-6-yl group, [1,2,4]triazolo[4,3-a]pyridin-7-yl group, thieno[3,2-c]pyridin-2-yl group, thieno[3,2-c]pyridin-3-yl group, thieno[3,2-c]pyridin-6-yl group, thieno[3,2-b]pyridin-2-yl group, thieno[3,2-b]pyridin-3-yl group, thieno[3,2-b]pyridin-5-yl group, thieno[3,2-b]pyridin-6-yl group, 1H-thieno[3,2-c]pyrazol-5-yl group, 1H-thieno[3,2-c]pyrazol-4-yl group, benzo[d]isoxazol-5-yl group, benzo[d]isoxazol-4-yl group, benzo[d]isoxazol-6-yl group, benzo[d]isoxazol-7-yl group, benzo[c]isoxazol-5-yl group, benzo[c]isoxazol-4-yl group, benzo[c]isoxazol-6-yl group, benzo[c]isoxazol-7-yl group, indolizin-7-yl group, indolizin-6-yl group, indolizine-8-yl group, 1,3-dihydroindol-5-yl group, 1,3-dihydroindol-4-yl group, 1,3-dihydroindol-6-yl group, 1H-pyrazolo[3,4-d]thiazol-5-yl group, 2H-isoindol-5-yl group, 2H-isoindol-4-yl group, [1,2,4]triazolo[1,5-a]pyrimidin-6-yl group, 1H-pyrazolo[3,4-b]pyrazin-5-yl group, 1H-imidazo[4,5-b]pyrazin-5-yl group, 7H-purin-2-yl group, 4H-chromen-6-yl group, and 4H-chromen-5-yl group (the aforementioned groups may be substituted with one of Xa or two or more of identical or different Xa). The substituent Xa represents a group as any one of oxo group, thioxo group, fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, 2-hydroxyethyl group, carboxymethyl group, 2-carboxyethyl group, N,N-dimethylcarbamoylmethyl group, hydroxyl group, methoxy group, 2-hydroxyethyloxy group, carboxymethyloxy group, 2-carboxyethyloxy group, N,N-dimethylcarbamoylmethyloxy group, amino group, methylamino group, dimethylamino group, 2-hydroxyethylamino group, carbamoylamino group, acetylamino group, furan-2-carboxyamino group, 2-hydroxyacetylamino group, 2-aminoacetylamino group, methylsulfonylamino group, (N,N-dimethylsulfamoyl)amino group, methanesulfonyl group, sulfamoyl group, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, carboxyl group, acetyl group, carbamoyl group, and N,N-dimethylcarbamoyl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In a particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C²′ represents carbon atom to which AR′ binds, C³′ represents carbon atom to which Rs′ binds, C⁴′ may be replaced with V′, and C⁵′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C²′ represents carbon atom to which AR′ binds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ may be replaced with V′, and C³′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

V′ represents nitrogen atom, or carbon atom substituted with Zx′, and Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group. Provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C³′ represents carbon atom to which AR′ binds, C⁵′ represents carbon atom to which Rs′ binds, and C²′, C⁴′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C³′ represents carbon atom to which AR′ binds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents nitrogen atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C³′ represents carbon atom to which AR′ binds, C⁴′ represents carbon atom to which Rs′ binds, C⁶′ represents carbon atom substituted with Zx′, and C²′ and C⁵′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C³′ represents carbon atom to which AR′ binds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents carbon atom substituted with Zx′, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, and N,N-dimethylsulfamoylamino group. Provided that when the substituted Zx′ contains amino group (NH), the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ represents any one of butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, and 2-(N-ethyl-N-phenylamino)ethyl group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

In another particularly preferred embodiment, the compound represented by the formula (III) satisfies all of the following requirements.

C³′ represents carbon atom to which AR′ binds, C⁴′ represents carbon atom to which Rs′ binds, C⁵′ represents carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, and C²′ and C⁶′ represent an unsubstituted ring-constituting carbon atom.

Zx′ represents any one of fluorine atom, methyl group, hydroxyl group, amino group, N-methylamino group, and N,N-dimethylamino group, provided that when Zx′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when the substituted Zx′ contains amino group, the amino group may be protected with Rp².

Rs′ represents —O-Rx′. Rx′ have the same meaning as that of Rc, provided that when Rc contains hydroxyl group, the hydroxyl group may be protected with Rp¹. p in Rc represents an integer of 2, and A⁴ represents a single bond or methylene. A⁵ represents —C(O)—, —C(S)—, or —S(O)₂—. Rd represents a group as any one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, benzyl group, 4-chlorophenylmethyl group, and 4-fluorophenylmethyl group. Re represents a group as any one of isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, phenyl group, 4-methylphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, cyclopentylmethyloxy group, cyclohexylmethyloxy group, phenyloxy group, 4-methylphenyloxy group, 4-chlorophenyloxy group, 4-fluorophenyloxy group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-t-butylamino group, N-cyclopropylamino group, N-cyclopentylamino group, N-cyclohexylamino group, N-phenylamino group, N-(4-methylphenyl)amino group, N-(4-chlorophenyl)amino group, N-(4-fluorophenyl)amino group, pyrrolidino group, piperidino group, and morpholino group.

AR′ represents any one of naphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 6-methoxynaphthalen-2-yl group, 6-(2-hydroxyethyloxy)naphthalen-2-yl group, 6-aminonaphthalen-2-yl group, 6-(N-methylamino)naphthalen-2-yl group, 6-(N,N-dimethylamino)naphthalen-2-yl group, 6-(2-hydroxyethylamino)naphthalen-2-yl group, benzo[b]furan-5-yl group, 2-methylbenzo[b]furan-5-yl group, 3-methylbenzo[b]furan-5-yl group, 2,3-dimethylbenzo[b]furan-5-yl group, benzo[b]thiophen-5-yl group, 2-methylbenzo[b]thiophen-5-yl group, 3-methylbenzo[b]thiophen-5-yl group, 2,3-dimethylbenzo[b]thiophen-5-yl group, 1H-indol-5-yl group, 2-methyl-1H-indol-5-yl group, 3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1H-indol-5-yl group, 1-methyl-1H-indol-5-yl group, 1,2-dimethyl-1H-indol-5-yl group, 1,3-dimethyl-1H-indol-5-yl group, 1,2,3-trimethyl-1H-indol-5-yl group, 1-ethyl-1H-indol-5-yl group, 1-ethyl-2-methyl-1H-indol-5-yl group, 1-ethyl-3-methyl-1H-indol-5-yl group, 1-ethyl-2,3-dimethyl-1H-indol-5-yl group, 1-propyl-1H-indol-5-yl group, 2-methyl-1-propyl-1H-indol-5-yl group, 3-methyl-1-propyl-1H-indol-5-yl group, 2,3-dimethyl-1-propyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-1H-indol-5-yl group, 1-(2-hydroxyethyl)-2-methyl-1H-indol-5-yl group, 1-(2-hydroxyethyl)-3-methyl-1H-indol-5-yl group, 2,3-dimethyl-1-(2-hydroxyethyl)-1H-indol-5-yl group, benzothiazol-6-yl group, 2-methylbenzothiazol-6-yl group, 2-methoxybenzothiazol-6-yl group, 2-aminobenzothiazol-6-yl group, 2-oxo-2,3-dihydrobenzothiazol-6-yl group, 2-oxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-2,3-dihydrobenzothiazol-6-yl group, 2-thioxo-3-methyl-2,3-dihydrobenzothiazol-6-yl group, quinolin-3-yl group, quinolin-6-yl group, 2-oxo-1,2-dihydroquinolin-6-yl group, benzo[d]isothiazol-5-yl group, 1H-indazol-5-yl group, 1-methyl-1H-indazol-5-yl group, 1-ethyl-1H-indazol-5-yl group, 1-propyl-1H-indazol-5-yl group, 1-(2-hydroxyethyl)-1H-indazol-5-yl group, 3-hydroxy-1H-indazol-5-yl group, 3-hydroxy-1-methyl-1H-indazol-5-yl group, 1-ethyl-3-hydroxy-1H-indazol-5-yl group, imidazo[1,2-a]pyridin-6-yl group, 1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-ethyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl group, 1-(2-hydroxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl group, isoquinolin-6-yl group, 1-oxo-1,2-dihydroisoquinolin-6-yl group, cinnolin-6-yl group, and benzoxazol-5-yl group. Provided that when AR′ contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when substituted AR′ contains amino group, the amino group may be protected with Rp².

Compound (I) of the present invention can be produced by, for example, employing the reactions according to the following various methods.

[Preparation Method 1] (Step a-1)

As shown in the following scheme 1:

a compound of the present invention represented by the formula (Ia′) wherein Y represents a lower alkyl group having 1 to 4 carbon atoms, and Rs, AR, and V on or in the aromatic ring (E) may be protected [hereinafter simply referred to as “Compound (Ia′)”], which falls within the scope of Compound (I) of the present invention, can be prepared by reacting a compound represented by the formula (II) [simply referred to as “Compound (II)” hereinafter] with a boronic acid derivative represented by the formula (IV) [hereinafter simply referred to as “Compound (IV)”]. n, C²′ to C⁶, Rs′, AR′, Y′ and G in the formulas have the same meanings as defined above. In the formula of Compound (IV), L¹ and L² independently represent hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms (e.g., methoxy group, ethoxy group, propoxy group, isopropoxy group, cyclohexyloxy group), or a substituted or unsubstituted phenyloxy group, or L¹ and L² bind to each other to represent a 5- or 6-membered cyclic ester of an arylboric acid (e.g., 9-borabicyclo[3,3,1]nonane, 1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane), which forms a ring containing boron atom [this ring may be saturated or unsaturated, may be a ring containing a heteroatom other than boron (e.g., oxygen atom), and may be further substituted].

Further, as shown in the following scheme 2:

an example of the method for preparing Compound (Ia′) includes a method of reacting a combination of a compound represented by the formula (V) [hereinafter simply referred to as “Compound (V)”] and a compound represented by the formula (VI) [hereinafter simply referred to as “Compound (VI)”].

Examples include a method of preparing Compound (Ia′) by performing the Suzuki reaction described in, for example, Jikken Kagaku Koza, 4th Edition (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 25, p. 403 with a combination mentioned either in the scheme 1 or scheme 2 or the both. A specific example includes a reaction of Compound (II) [or Compound (V)] with Compound (IV) [or Compound (VI)] in a solvent in the presence of a commercially available palladium catalyst or a catalyst prepared from a palladium complex and a ligand, and a base.

As the palladium catalyst, a commercially available catalyst such as tetrakis(triphenylphosphine)palladium, tetrakis(methyldiphenylphosphine)palladium, dichlorobis(triphenylphosphine)palladium, dichlorobis(tri-o-tolylphosphine)palladium, dichlorobis(tricyclohexylphosphine)palladium, dichlorobis(triethylphosphine)palladium, palladium acetate, palladium chloride, bis(acetonitrile)palladium chloride, tris(dibenzylideneacetone)dipalladium and bis(diphenylphosphinoferrocene)palladium chloride may be purchased and added to the reaction system, per se, or a catalyst may be added which is separately prepared from palladium acetate, tris(dibenzylideneacetone)dipalladium or the like and arbitrary ligands and isolated. Further, a catalyst considered to actually participate in the reaction may also be prepared by mixing palladium acetate, tris(dibenzylideneacetone)dipalladium or the like and arbitrary ligands in the reaction system. The valence of palladium may be 0 or may be +2. Examples of the ligand include phosphine ligands such as trifurylphosphine, tri(o-tolyl)phosphine, tri(cyclohexyl)phosphine, tri(t-butyl)phosphine, dicyclohexylphenylphosphine, 1,1′-bis(di-t-butylphosphino)ferrocene, 2-dicyclohexylphosphino-2′-dimethylamino-1,1′-biphenyl and 2-(di-t-butylphosphino)biphenyl and phosphine mimic ligands such as imidazol-2-ylidenecarbenes. Chemical equivalents of the palladium catalyst may be one equivalent or a catalytic amount, and the amount may preferably be 0.01 to 20.0 mol %, and most preferably be 0.10 to 10.0 mol %.

Examples of the base include sodium carbonate, potassium carbonate, cesium carbonate, cesium fluoride, potassium fluoride, potassium phosphate, potassium acetate, triethylamine, potassium hydroxide, sodium hydroxide, sodium methoxide, lithium methoxide and the like. The reaction temperature is, for example, preferably 20° C. to 150° C., and particularly preferable examples include 20° C. to 120° C.

The reaction system may be either a two-phase system of water and an organic solvent, or a homogeneous system of a water-containing organic solvent or an organic solvent. As for the organic solvent, examples include uses of hydrocarbon-type solvents such as toluene, xylene and hexane, halogen-type solvents such as methylene chloride, sulfoxide-type solvents such as dimethyl sulfoxide, amide-type solvents such as dimethylformamide, ether-type solvents such as tetrahydrofuran, dioxane and diglyme, alcohol-type solvents such as methanol and ethanol, nitrile-type solvents such as acetonitrile, ketone-type solvents such as acetone and cyclohexanone, ester-type solvents such as ethyl acetate, heterocyclic-type solvents such as pyridine and the like. Two or more kinds of organic solvents may be mixed and used.

For the reaction conditions, Miyaura, N., Suzuki, A., Chemical Review, 1995, vol. 95, p. 2457; Snieckus, V., Chemical Review, 1990, vol. 90, p. 879 and the like and references cited therein can be referred to.

When hydroxyl group or amino group reactive under the aforementioned reaction conditions or inhibiting the reactions exists in the group AR′, Rs′ or V′ in the aromatic ring (E′), this substituent is preferably protected.

When a protective group of hydroxyl group or amino group exist in the group AR′, Rs′ or V′ in the aromatic ring (E′) of the compound (Ia′) prepared as described above, such a protective group can be eliminated during or after the preparation of Compound (Ia′) to convert the compound into Compound (I) of the present invention. As for selection, introduction and deprotection of these protective groups of hydroxyl group and amino group, ordinary chemical publications, for example, Protective Groups In Organic Synthesis THIRD EDITION, John Wiley & Sons) and references cited therein can be referred to.

[Preparation Method 1] (Step a-2)

As Compound (IV), a compound commercially available as a reagent may be used, or as shown in the following scheme 3:

the compound can be produced from Compound (VI), which is commercially available or can be synthesized by a known method or a similar method thereto, according to the method described in the aforementioned reference (Chemical Review, vol. 95, p. 2457, 1995) or the method described in Satoh, Y. et al., SYNTHESIS, p. 1146, 1994 or according to the references cited therein.

For example, examples include a method of preparing Compound (VI) by converting Compound (VI) into a lithio-compound using an alkyl lithium such as n-butyl lithium and t-butyl lithium, then reacting the product with a trialkyl borate and treating the product with a mineral acid such as hydrochloric acid, sulfuric acid, and phosphoric acid; and a method of to preparing Compound (VI) by performing a cross-coupling reaction of Compound (VI) and an (alkoxyl)diboron in the presence of a palladium catalyst and a base.

An example of the preparation method of Compound (V) includes a method of subjecting Compound (II) to a reaction similar to that of the aforementioned Step a-2, as shown in the following scheme 4:

[Preparation Method 1] (Step b)

As shown in the following scheme 5:

a compound represented by the formula (IIh) (hereinafter simply referred to as “Compound (IIh)”), which correspond to the compounds (II) wherein G represents a halogen atom such as chlorine atom, bromine atom or iodine atom, can be prepared by halogenating a compound represented by the formula (VII) [this compound is simply referred to as “Compound (VII)”], which is commercially available or can be prepared by a known method or a method similar thereto. In the formula of Compound (IIh), the group Hal represents a halogen atom, which may be any of chlorine atom, bromine atom and iodine atom. As for the halogenation, examples of chlorination include a preparation method described in ordinary publications in the filed of chemistry, for example, Shin Jikken Kagaku Koza (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 354. Examples of the method include a method utilizing chlorine (Cl₂), a method utilizing sulfuryl chloride, and the like. Examples of bromination include a preparation method described in ordinary publications in the filed of chemistry, for example, Shin Jikken Kagaku Koza (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 354. Examples of the method include a method utilizing bromine (Br₂), a method utilizing N-bromosuccinimide, and the like. Examples of iodination include a preparation method described in ordinary publications in the filed of chemistry, for example, Shin Jikken Kagaku Koza (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 423. Examples of the method include a method utilizing iodine (I₂), a method utilizing potassium triiodide, and the like.

[Preparation Method 1] (Step c)

As shown in the following scheme 6:

a compound represented by the formula (IIs) (this compound is hereinafter simply referred to as “Compound (IIs)”), which corresponds to Compound (II) wherein G represents mesylate group, triflate group, or an arenesulfonate group, can be prepared by converting a compound represented by the formula (VIII) (this compound is simply referred to as “Compound (VIII)”), which is commercially available or can be prepared by a known method or a method similar thereto, into a sulfonic acid ester. In the formula of Compound (IIs), the group Su represents methanesulfonyl group, trifluoromethanesulfonyl group, or arenesulfonyl group of which aromatic ring may be substituted with one of T¹ or two or more of identical or different T¹. Examples of the method for the conversion into sulfonic acid ester include a preparation method described in ordinary publications in the filed of chemistry, for example, Shin Jikken Kagaku Koza (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 1793. Examples of the method include a method utilizing sulfonyl chloride, a method utilizing sulfonic anhydride, and the like.

[Preparation Method 2] (Step d)

As shown in the following scheme 7:

a compound represented by the formula (Ib′) wherein Y represents hydrogen atom, and Rs, AR, and V on or in the aromatic ring (E) may be protected (this compound is hereinafter simply referred to as “Compound (Ib′)”), which constitutes a part of the scope of Compound (I) of the present invention, can be prepared by hydrolyzing Compound (Ia′) so as to convert the group OY′ into hydroxyl group.

For the reaction of converting Compound (Ia′) into Compound (Ib′), in general, the compound is preferably reacted in a base. Further, for the reaction of converting Compound (Ia′) to Compound (Ib′), in general, the compound is preferably reacted in an inert medium that does not inhibit the reaction, preferably a polar solvent.

Examples of the base used in the above reaction include, for example, alkali metal bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide and potassium t-butoxide and organic bases such as triethylamine. As for amounts of the bases, generally 1 to 20 moles, preferably 1 to 10 moles, for alkali metal bases, or 1 to a large excess moles for organic bases based on Compound (Ia′).

Examples of the polar solvent include water, methanol, ethanol, tetrahydrofuran, dioxane and the like, and these solvents may be used as a mixture as required. As the reaction temperature, an appropriate temperature of, for example, from room temperature to a refluxing temperature of solvent is chosen. The reaction time is, for example, generally 0.5 to 72 hours, preferably 1 to 48 hours, when an alkali metal base is used, or generally 5 hours to 14 days when an organic base is used. Since progress of the reaction can be monitored by thin layer chromatography (TLC), high performance liquid chromatography (HPLC) or the like, the reaction can generally be terminated appropriately so as to maximize the yield of Compound (Ib′).

For collection of Compound (Ib′) obtained as described above from the reaction solution as a free carboxylic acid, operations may preferably be carried out by, when the polar solvent is a water-soluble solvent, evaporating the solvent, neutralizing the residue with an inorganic acid such as aqueous hydrochloric acid, dissolving the residue in a water-insoluble solvent, then washing the solution with a weakly acidic aqueous solution, water or the like, and evaporating the solvent. When the polar solvent is a water-insoluble solvent, operations may preferably carried out by neutralizing the reaction solution with an inorganic acid, washing the solution with a weakly acidic aqueous solution, water or the like, and then evaporating the solvent.

Further, when Compound (Ib′) forms a salt with the base used after the reaction to give a solid, the salt of Compound (Ib′) can be obtained by isolation and purification of the solid in a conventional manner.

When a protective group of hydroxyl group or amino group exists in the group AR′, Rs′ or V′ in the aromatic ring (E′) of Compound (Ia′) prepared as described above, Compound (Ia′) can be converted into Compound (I) of the present invention by removing the protective group during or after the preparation of Compound (Ia′).

[Preparation Method 3] (Step e)

As shown by the following scheme 8:

a compound represented by the formula (Ic′) [hereinafter simply referred to as “Compound (Ic′)”] as Compound (I) of the present invention wherein the group Y represents Y″, and Rs, AR, and V in the aromatic ring (E) may be protected, can be produced by esterifying the carboxyl group (COOH) of Compound (Ib′) in a conventional manner. In the formula of Compound (Ib′), Y″ represents a lower alkyl group having 1 to 4 carbon atoms, a —(CH₂)_(m)NR¹⁸R¹⁹ group, or —C(R²⁰)₂OC(O)A³R²¹.

Examples of the method for producing Compound (Ic′) include a method of allowing Compound (Ib′) to react with an inorganic halide without solvent or in an inert solvent to convert the compound into an acid halide and then allowing the acid halide per se or the same dissolved in an inert solvent to react with an excess amount of hydroxide of the targeted Y″. Examples of the inorganic halide used in this method include thionyl chloride, phosphoryl chloride, phosphorus pentachloride, phosphorus trichloride and the like, and thionyl chloride is a preferred example. Examples of an amount used include generally an equimolar to a large excess amount, preferably 1.5 to 5 moles based on Compound (Ib′). Examples of the inert solvent used in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, ethers such as tetrahydrofuran and dioxane, and benzene compounds such as benzene, toluene, xylene and chlorobenzene. These solvents can be used, for example, each alone or as a mixed solvent. In order to promote the reaction, a catalytic amount of N,N-dimethylformamide may be added. As a reaction temperature, an appropriate temperature of from room temperature to a refluxing temperature of the solvent is generally chosen. Examples of the reaction time include generally 0.5 to 24 hours, preferably 1 to 6 hours.

Examples of the inert solvent used for the reaction with hydroxide of the targeted Y″ include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, ethers such as tetrahydrofuran and dioxane, and benzene compounds such as benzene, toluene, and xylene. The reaction can also be performed with an excess amount of the hydroxide of the targeted Y″ without using a solvent. As the reaction temperature, an appropriate temperature of from −10° C. to room temperature is chosen. Examples of the reaction time include generally 0.5 to 24 hours, preferably 0.5 to 6 hours.

Other methods for producing Compound (Ic′) include, for example, the “esterification using an alcohol” described in Shin Jikken Kagaku Koza (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 1002, “esterification using an O-alkylating agent”, ibid, the same volume, p. 1002, “esterification using an alkyl halide”, ibid, the same volume, p. 1008, “esterification reaction using a dehydrating agent”, ibid, vol. 22, p. 45 and the like.

When hydroxyl group or amino group reactive under the aforementioned reaction conditions or inhibiting the reactions exists in AR′, Rs′ or V′ in the aromatic ring (E′), this substituent is preferably protected.

When a protective group of hydroxyl group or amino group exist in AR′, Rs′ or V′ in the aromatic ring (E′) of the compound (Ic′) prepared as described above, such a protecting group can be eliminated during or after the preparation of Compound (Ic′) to convert the compound into Compound (I) of the present invention.

[Preparation Method 4]

As shown in the following scheme 9:

a compound represented by the formula (Id′) (hereinafter this compound is simply referred to as “Compound (Id′)”) as Compound (I) of the present invention wherein n in the methylene moiety is an integer of 2, and wherein Rs, AR, and V in the aromatic ring (E) may be protected, can also be prepared by the method shown below.

[Preparation Method 4] (Step f)

Compound (Id′) can be prepared by reducing the double bond of a compound represented by the formula (IX) (hereinafter this compound is simply referred to as “Compound (IX)”) using a reduction reaction described in ordinary publications in the filed of chemistry. Examples of the reaction include a method of converting the double bond of Compound (IX) into a single bond by hydrogenation using a hydrogen source such as hydrogen gas, ammonium formate, and hydrazine hydrate in a single solvent or a mixed solvent of alcoholic-type solvents such as methanol, ester-type solvents such as ethyl acetate in the presence of a catalyst such as palladium/carbon powder, platinum oxide (PtO₂), and activated nickel.

When hydroxyl group or amino group reactive under the aforementioned reaction conditions or inhibiting the reactions exists in AR′, Rs′ or V′ in the aromatic ring (E′), this substituent is preferably protected.

When a protective group of hydroxyl group or amino group exist in AR′, Rs′ or V′ in the aromatic ring (E′) of the compound (Id′) prepared as described above, such a protecting group can be eliminated during or after the preparation of Compound (Id′) to convert the compound into Compound (I) of the present invention.

[Preparation Method 4] (Step g)

Compound (IX) can be prepared from a compound represented by the formula (III) [hereinafter this compound is simply referred to as “Compound (III)”]. Examples of the preparation method include a method utilizing the Horner-Emonds reaction described in Shin Jikken Kagaku Koza (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 14, p. 238. Specifically, the compound can be obtained by reacting Compound (III) with a commercially available dialkylphosphonoacetic acid ester in an inert solvent, for example, an alcohol-type solvent such as methanol and ethanol or ether-type solvent such as tetrahydrofuran and dimethoxyethane in the presence of a base such as sodium hydride and sodium alkoxide. As the reaction temperature, an appropriate temperature of from −10° C. to a refluxing temperature of a solvent is generally chosen, and preferred examples include a temperature of from 0° C. to room temperature. The reaction time is generally 1 to 16 hours, preferably 2 to 8 hours. Since progress of the reaction can be monitored by thin layer chromatography (TLC), high performance liquid chromatography (HPLC) or the like, the reaction can generally be terminated appropriately so as to maximize the yield of Compound (IX).

[Preparation Method 4] (Step a)

As shown in the following scheme 10:

Compound (III) can be prepared by introducing the substituent AR′ into a compound represented by the formula (X) [hereinafter this compound is simply referred to as “Compound (X)”] according to any of the methods described in the step a-1 of the preparation method 1 mentioned above.

[Preparation Method 5]

As shown in the following scheme 11:

a compound represented by the formula (Ie′) [hereinafter this compound is simply referred to as “Compound (Ie′)”], as Compound (I) of the present invention wherein n in the methylene moiety is an integer of 1, Y represents hydrogen atom, and Rs, AR, and V in the aromatic ring (E) may be protected, can also be prepared by the method shown below.

[Preparation Method 7] (Step d)

Specifically, Compound (Ie′) can be prepared by hydrolyzing nitrile group of a compound represented by the formula (XI) [hereinafter this compound is simply referred to as “Compound (XI)”] into carboxyl group according to a method similar to the method shown in the step d of the preparation method 2 mentioned above.

When a protective group of hydroxyl group or amino group exist in AR′, Rs′ or V′ in the aromatic ring (E′) of the compound (Ie′) prepared as described above, such a protecting group can be eliminated during or after the preparation of Compound (Ie′) to convert the compound into Compound (I) of the present invention.

[Preparation Method 5] (Step h)

Compound (XI) can be produced from Compound (III) mentioned above. For example, Compound (III) is reacted with a trimethylsilyl cyanide using a Lewis acid, particularly zinc iodide, as a catalyst in an inert solvent such as tetrahydrofuran as described in Jikken Kagaku Koza, 4th Edition (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 20, p. 445. Then, the reduction reaction using a hydrosilane described in Jikken Kagaku Koza, 4th Edition (edited by Chemical Society of Japan, published by Maruzen Co., Ltd.), vol. 26, p. 197 is performed. Examples of the method of the reduction reaction include a method of performing the reduction with a hydrosilane such as triethylsilane and a protonic acid such as trifluoroacetic acid or a Lewis acid such as boron trifluoride in a halogenated solvent such as dichloromethane.

The preparation method of Compound (I) is not limited to the methods described herein. For example, the compounds of the present invention can be produced by modifying or converting a substituent of a compound serving as a precursor of the compounds according to a method or a combination of methods described in ordinary publications in the filed of chemistry.

Examples of the preparation method for Compound (I) of the present invention which contains an asymmetric carbon in the substituent Rs include a method of using a starting material in which a moiety corresponding to the asymmetric carbon in the substituent Rs is already optically active, which is commercially available (or can be prepared by a known method or a method similar thereto). A method is also available in which the compound of the present invention or a precursor thereof is separated as an optically active isomer in a conventional manner. Examples of such method include, for example, a method utilizing high performance liquid chromatography (HPLC) using a chiral column, a method comprising condensation with an optically active regent to form a diastereomer, successive separation and purification, followed by decomposition. When a precursor is separated to obtain an optical isomer, optically active Compound (I) of the present invention can then be prepared by performing the aforementioned preparation methods.

When Compound (I) of the present invention contains an acidic functional group such as carboxyl group or phenolic hydroxyl group, the compound can be converted into pharmaceutically acceptable salt (e.g., inorganic salts with sodium, ammonia and the like, or organic salts with triethylamine and the like) by a known means. For example, when an inorganic salt is to be obtained, it is preferable to dissolve Compound (I) of the present invention in water containing at least 1 equivalence of hydroxide, carbonate, bicarbonate or the like corresponding to a desired inorganic salt. For the reaction, an inactive water-miscible organic solvent such as methanol, ethanol, acetone, and dioxane may be mixed. For example, by using sodium hydroxide, sodium carbonate, or sodium hydrogencarbonate, a solution of sodium salt can be obtained.

When Compound (I) of the present invention contains a basic functional group such as amino group, or when Compound (I) of the present invention contains an aromatic ring which itself has properties of base (e.g., pyridine ring), the compound can be converted into a pharmaceutically acceptable salt (e.g., salt with inorganic acids such as hydrochloric acid and sulfuric acid, or salts with organic acids such as acetic acid and citric acid) by a known means. For example, when an inorganic salt is to be obtained, it is preferable to dissolve Compound (I) of the present invention in water containing at least 1 equivalence of a desired inorganic acid. For the reaction, an inactive water-miscible organic solvent such as methanol, ethanol, acetone, and dioxane may be mixed. For example, by using hydrochloric acid, a solution of hydrochloride can be obtained.

When a solid salt is desired, a solution may be evaporated, or a water-miscible organic solvent having polarity to some extent, such as butanol or ethyl methyl ketone, can be added to obtain a solid salt thereof.

The various compounds disclosed by the present invention can be purified by known methods such as recrystallization, and variety of chromatography techniques (column chromatography, flash column chromatography, thin layer chromatography, high performance liquid chromatography).

Compound (I) of the present invention and pharmaceutically acceptable salts thereof have an action of suppressing the production of both of prostaglandins and leukotrienes. The action of suppressing the production of prostaglandins and/or leukotrienes includes, for example, an action of suppressing PGE₂ production, observed when cultured cells of MG-63 which is a human osteosarcoma cell line are stimulated with IL-1β and/or PGD₂ and LTB₄ production observed when cultured cells of RBL-2H3 which is a rat mastocytoma cell line are stimulated with IgE, by 10% or more, preferably 30% or more, most preferably 50% or more, compared with a positive control at a concentration of the compound not having cytotoxicity. As for a mode of action at a molecular level, it is considered that the compound of the present invention inhibits both of COX-1 and/or COX-2, which produce prostaglandins, and 5-LO, which produces leukotrienes. It is also considered that the compound of the present invention suppresses the production of arachidonic acid by inhibiting enzymatic activity of type 2A, 4, or 5 PLA₂ involved in prostaglandin and leukotrien production.

It is considered that, in these molecular action mechanisms, Compound (I) of the present invention inhibits the enzymatic activity of type 4 PLA₂. For the judgment, for example, the enzyme inhibitory action against type 4 PLA₂ can be examined, and known methods for measuring the enzymatic activity of type 4 PLA₂ are preferably utilized [Clark et al., Proceeding of National Academy of Science USA (Proc. Natl. Acad. Sci. USA), 1990, vol. 87, p. 7708; Gronich et al., Biochemical Journal (Biochem. J.), 1990, vol. 271, p. 37; Clark et al., Cell, 1991, vol. 65, p. 1043; Kramer et al., Journal of Biological Chemistry (J. Biol. Chem.), 1991, vol. 266, p. 5268]. The type 4 PLA₂ inhibitory action of the compounds of the present invention can be elucidated by employing these methods.

Compounds (I) of the present invention and pharmaceutically acceptable salts thereof inhibited mouse inflammatory edema, allergic edema, acetic acid writhing reaction, and rat adjuvant arthritis by oral administration at a dose of 0.1 to 500 mg/kg, and caused no death of the mice by oral administration at a dose of 500 mg/kg/day for 3 days. Therefore, they are safe compounds as drugs for mammals, preferably humans, pets or companion animals such as dogs and cats, and farm animals, and they are useful substances as active ingredients of medicaments. Preferred examples of the medicaments for mammals, preferably humans, pets or companion animals such as dogs and cats, and farm animals include agents for prophylactic and/or therapeutic treatment of various conditions, various diseases, and pathological conditions in which an acute or chronic inflammatory reaction resulted from production of prostaglandin and/or leukotriene is observed, specifically inflammatory diseases, allergic diseases, autoimmune diseases, and pain.

More specifically, the conditions or diseases include arthritis, chronic rheumatoid arthritis, malignant rheumatoid arthritis, juvenile rheumatoid arthritis, Felty's syndrome, adult Still's disease, osteoarthritis, synovitis, gout, slack of artificial joint implant, fervescence, common cold, algesia, burn, thermal injury, keloplasty, menstrual pain, dysmenorrhea, menstrual cramp, allergic reaction, allergic contact hypersensitivity, allergic rhinitis, pollinosis, allergic conjunctivitis, hypersensitivity pneumonitis, allergic bronchopulmonary mycosis, emphysema, acute respiratory distress syndrome, asthma, bronchitis, chronic obstructive pulmonary disease, chronic bronchitis, pulmonary emphysema, diffuse panbronchiolitis, respiratory obstruction, graft versus host syndrome, urticaria, ultraviolet radiation dermatitis, atopic dermatitis, cancer, myelogenous leukemia, sarcomata, brain tumor, cachexia, tissue ulcer, digestive ulcer, gastritis, acute and chronic pancreatitis, regional enteritis, ulcerative colitis, diverticulitis, recurrent gastroenteric disorder, gastroenteric bleeding, inflammatory bowel disease, Crohn's disease, intestinal tract type Behcet's disease, infectious enteritis, ischemic enteritis, radiation enteritis, drug-induced enteritis, irritable bowel syndrome, hepatic diseases (hepatopathies, liver failures) such as acute hepatitis, fulminant hepatitis, chronic hepatitis, hepatic cirrhosis, fatty liver, alcoholic liver injury, drug liver injury (drug-induced hepatitis), congestive hepatitis, autoimmune hepatitis, primary biliary cirrhosis and hepatic porphyria, coagulation, anemia, ankylosing spondilitis, restenosis, periodontosis, epidermolysis bullosa, atherosclerosis, aortic aneurysm, periarteritis nodosa, congestive cardiac failure, arrhythmia, myocardial infarction, cerebral infarction, attack, cerebral ischemia, head injury, spinal cord injury, myelopathic muscular atrophy, neuralgia, neurodegenerative disease, Alzheimer's disease, Lewy body disease, Shy-Drager syndrome, Reye's syndrome, progressive supranuclear palsy, progressive multifocal leukoencephalopathy, normal pressure hydrocephalus, subacute sclerosing panencephalitis, frontal lobe type dementia, acute anterior poliomyelitis (poliomyelitis), poliomyelitis neurosis, viral encephalitis, Creutzfeldt-Jakob disease, Kuru disease, bovine spongiform encephalopathy (mad cow disease), scrapie, epilepsy, cerebral amyloid angiopathy, autoimmune disease, Huntington's disease, Parkinson's disease, migraine, depression, mania, manic-depressive psychosis, hereditary cerebellar ataxia, peripheral neuropathy, glaucoma, pain, gingivitis, postoperative pain, amyotrophic lateral sclerosis, osteoporosis, multiple sclerosis, ocular angiogenesis, cornea damage, macular degeneration, conjunctivitis, abnormal wound healing, sprain or strain of muscle or joint, tendinitis, skin disease, psoriasis vulgaris, pustular psoriasis, erythroderma psoriaticum, arthritic psoriasis, myasthenia gravis, multiple myositis, myositis, bursitis, diabetes mellitus, tumor invasion, tumor growth, tumor metastasis, cornea scar, scleritis, immunodeficiency disease, pachydermia, eosinophilic fasciitis, sepsis, endotoxin shock, premature delivery, hypoprothrombinemia, hemophilia, thyroiditis, sarcoidosis, Behcet's syndrome, hypersensitivity, renal disease, rickettsial infectious disease, protozoal disease, reproduction disease, sepsis shock and the like. Other specific conditions and diseases include toothache, pain after tooth extraction, back or low back pain, periarthritis humeroscapularis, cervico-omo-brachial syndrome, tenosynovitis, acute upper respiratory inflammation, herpes zoster, fibrosis, pulmonary fibrosis, pneumoconiosis, chronic interstitial pneumonia, granulomatous interstitial pneumonia, fibrosing interstitial pneumonia, renal fibrosis, nephropyelitis, various types of secondary contracted kidney, glomerular nephritis, chronic nephritis, glomerulosclerosis, hepatic fibrosis, cardiac fibrosis after myocardial infarction, idiopathic cardiomyopathy, pancreatic sclerosis, pancreatic fibrosis, pancreatolithiasis, Takayasu's arteritis, chronic thyroiditis, dermatomyositis, multiple myositis, myelofibrosis, Banti disease, retroperitoneal fibrosis, various radiation injuries and the like. Further, the medicament comprising Compound (I) of the present invention as an active ingredient can be used for the aforementioned conditions or diseases of mammals, preferably humans, pets or companion animals such as dogs and cats or farm animals together with or in combination with one or more kinds of other prophylactic or therapeutic drugs.

Examples of the drugs that can be used together or in combination include, for example, the following drugs: immunomodulation-type antirheumatic drugs and antimetabolite used as therapeutic drugs for rheumatoid arthritis, specifically, gold preparations, bucillamine, lobenzarit, salazosulfapyridine, methotrexate, azathiopurin, mizoribine, leflunomide, tacrolimus, cyclosporin and the like and preparations containing the same; anti-cytokine antibody preparations directed to cytokines such as interleukin (IL) 1, IL-6, and tumor necrosis factor (TNF)-α or preparations of soluble receptors for those cytokines, which are biological preparations, specifically, infliximab, etanercept and the like and preparations containing the same; steroid preparations, specifically, dexamethasone, betamethasone, prednisolone, fluticasone, beclometasone and the like and preparations containing the same; bronchodilators used as therapeutic agents for chronic bronchial asthma, specifically, salmeterol and salbutamol, which are adrenalin β2 stimulants, ipratropium, which is an anticholinergic drug, and the like and preparations containing the same; therapeutic drugs for allergic diseases, for example, theophyline, which is a xanthine analogue drug, and the like, fexoquinadine, epinastatine, cetirizine, ketotifen, disodium cromoglycate, pemirolast and the like, which are antiallergic agents, fexoquinadine, cetirizine and the like, which are antihistaminic agents, and preparations containing the same; irinotecan, 5-fluorouracil and the like, which are antitumor agents, and preparations containing the same. Further, the medicament comprising Compound (I) of the present invention as an active ingredient is used, for example, together with or in combination with radiotherapy.

In order to use Compound (I) of the present invention or pharmaceutically acceptable salts thereof for the medicaments described above, an effective amount of Compound (I) of the present invention or a pharmaceutically acceptable salt thereof, per se, may be used, or the substance may be mixed with a pharmaceutically acceptable carrier to form a pharmaceutical composition. The carrier may be, for example, a suspending agent such as carboxymethylcellulose, or purified water, physiological saline or the like, if desired. Other known carriers can also be used. Examples include a method of dissolving Compound (I) of the present invention or a pharmaceutically acceptable salt thereof in purified water containing 0.5% carboxymethylcellulose and using the solution.

Examples of formulations for preparing the aforementioned pharmaceutical composition include tablet, powder, granule, syrup, suspension, capsule, and injection. For the manufacture of these formulations, various carriers suitable for these preparations are used. For example, examples of the carrier for oral preparations include excipients, binders, lubricants, fluid accelerators, and colorants.

When the compound of the present invention is formulated as a parenteral preparation such as an injection, water for injection, physiological saline, glucose aqueous solution, vegetable oil for injection, propylene glycol, polyethylene glycol and the like can generally be used as a diluent. Disinfectants, antiseptics, stabilizers, isotonic agents, soothing agents and the like may be further added, as required.

When the compound of the present invention is administered to a mammal, e.g., human, the compound can be administered in the form of a tablet, a powder, a granule, a suspension, a capsule or the like. The compound can also be parenterally administered in the form of a suppository, a gel, a lotion, an ointment, a cream, or a spray. A dose thereof varies depending on a disease to be applied, administration route, age, weight, degree of symptom of a patient and the like. Examples of the dose include generally an administration at a dose of 1 to 1,000 mg per day for an adult once to three times a day. Every day administration for a period of several days to two months is commonly applied. The daily dose and the administration period may be increased or decreased depending on symptoms of a patient.

Fibrosis, which is a disease characterized by fibrosing of tissues, is known as a severe disease which is often mortal. Fibrosing of tissues is caused by proliferation of interstitial cells, which represented by fibroblasts, and production of extracellular matrix such as collagen. Fibrosing is considered a repair mechanism against tissue affections in organs. Excessive fibrosing causes fibrosing diseases of organs, and further progression of fibrosing causes sclerotic diseases. Many of such sclerotic diseases are intractable, progressive and irreversible. Although fibrosing varies in various organs, etiological hypotheses of fibrosing have many similarities. That is, a certain inflammatory lesion precedes, and in its healing process, various kinds of cytokines and growth factors are produced mainly from immunocompetent cells and platelets as well as interstitial cells such as fibroblasts themselves involved in the healing, and activated to cause deposition of extracellular matrix (Takehara, Molecular Medicine, 2001, vol 38, p. 854).

Among fibroses, pulmonary fibrosis is one of the representative diseases. Pulmonary fibrosis is a disease in which disruption of alveolar structure is caused by chronic inflammation and increase of collagenic fibers in alveolar walls, and which eventually leads to respiratory failure and death. For example, pulmonary fibrosis occurs following infectious pneumonia and the like. Examples of the infectious pneumonia include severe acute respiratory syndrome (SARS) and influenzal pneumonia. It has been reported that, in SARS, in particular, severe inflammation is caused in pulmonary stroma, and as a result, it highly likely to develop into pulmonary fibrosis (Antonino et al., Radiology, 2003). In addition, pulmonary fibrosis is also caused by various medicaments.

In recent years, with increase of medicaments used for diagnosis, prophylactic and therapeutic treatments of various kinds of diseases, drug-induced pulmonary fibrosis caused by such drugs is increasing. Drug-induced pulmonary fibrosis is a severe disease that eventually leads to death, and it causes serious problems in therapeutic treatments of various diseases. Therefore, prophylactic and therapeutic treatments of drug-induced pulmonary fibrosis constitute a particularly important subject of concern.

Against drug-induced pulmonary fibrosis, steroid therapy is currently used. However, effective rate of the steroid therapy is low and the effect is only partial and transient, and thus lesions often remain [Igaku no Ayumi, 2001, vol. 197, p. 313]. Further, side effect of steroid agents and acute aggravation due to decrease of doses or termination of their administrations are also often observed, which remains clinically far unsatisfactory level.

As a recent finding, it was reported that administration of pirfenidone was effective against pulmonary fibrosis in clinical tests in the United States (Raghu et al., American Journal of Respiratory and Critical Care Medicine, 1999, vol. 159, p. 1061) and Japan (Nagai et al., Internal Medicine, 2002, vol. 41, p. 1118). However, development of novel prophylactic and/or therapeutic agents highly effective for these diseases is desired at all events.

The medicament provided by the present invention is useful as a medicament containing a type 4 PLA₂ inhibitor as an active ingredient for prophylactic and/or therapeutic treatment of fibrosis, preferably pulmonary fibrosis, further preferably drug-induced pulmonary fibrosis.

As described above, fibrosis, in particular, pulmonary fibrosis, is a severe disease and is an important object of prophylactic and/or therapeutic treatment. As for pulmonary fibrosis, more than 100 kinds of factors including toxic gases and various medicaments have been elucidated as the causes of early alveolopathy. As described above, with the increase of medicaments used for diagnosis, prophylactic and therapeutic treatments of various kinds of diseases, drug-induced pulmonary fibrosis caused by such drugs is increasing.

As for drug-induced pulmonary fibrosis, causality between expression of pathological conditions such as coughing, difficulty of breathing, or fervescence and the administration of medicaments is suspected, and it is considered that a diffuse interstitial shadow appears on a thoracic X-ray photograph simultaneously with or slightly after the administration of medicaments.

As medicaments reported to cause drug-induced pulmonary fibrosis, anticancer agents, anti-rheumatic agents, immunosuppressants, antibiotics, chemotherapeutants, antihypertensive agents, diuretics, anti-inflammatory/analgesic agents, biologics, Chinese medicines are known (Inooka et al., Therapeutics, 1995, vol. 29, p. 1295). Typical medicaments are shown in Table 1.

TABLE 1 Classification Examples of agent 1) Anticancer agent, Peplomycin, bleomycin, cychlophosphamide, nitrosourea, immunosuppressant busulfan, methotrexate, azathioprine, mitomycin-C, tegafur, carmofur, tegafur/uracil preparation, cisplatin, doxorubicin, 6-mercaptopurine, daunomycin, vincristine, vinblastine, vindesine, procarbazine, neocarzinostatin, melphalan, thiotepa, nimustine, cytarabine, zinostatin stimalamer, chlorambucil, carmustine, lomustine, semustine, teniposide, etoposide, Taxol, taxotere, irinotecan, gefitinib, tamoxifen and the like. 2) Antihypertensive α-methyldopa, trichlormethiazide, hydrochlorothiazide, agent, diuretic enalapril, hexamethonium, mecamylamine, pentolinium, practolol, pindolol, propranolol, acebutolol, hydralazine 3) Antibiotic, Cephem antibiotics (cephaloridine, cephalothin, chemotherapeutant cephalexin, cefradine, cefazolin, cefaclor, cefmenoxime, cefmetazole, cefoperazone, cefotiam, cefroxadin, ceftizoxime, latamoxef and the like), tetracyclines (minocycline, oxycycline), antituberculous agents (isoniazid, paraaminosalicylic acid, rifampicin, streptomycin), penicillin antibiotics (ampicillin, piperacillin, vastcillin, pentcillin, amoxicillin), aminoglycoside antibiotics (streptomycin), macrolide antibiotics (midecamycin), phosphomycin, aminoglycosides (tobramycin, Micromycin), new quinolone drugs (enoxacin, ofloxacin, norfloxacin), antifungal agents (amphotericin) and the like 4) Others Inhalants (cromoglicic acid and the like), gold preparations (aurothiomalic acid and the like), psychotropic agents and nervines (aminotriptyline, diphenylhydantoin, carbamazepine, phenobarbital, valproate salt, imipramine, mephenesin, meprobamate), antiphlogistic and analgesics (naproxen, acetaminophen, acetylsalicylic acid, phenacetin, diclofenac, loxoprofen, fenbufen, nabumetone, aluminoprophen and the like), antiarrhythmic agents (amiodarone, procainamide, aprindine), antidiabetic agents (chlorpropamide), antithyroid agents (thiouracil), proteolytic enzymes (serrapeptidase), antiparkinsonic agents (levodopa, bromocriptine), antirheumatic agents (bucillamine, auranofin, actarit), sho-saiko-to, chai-ling-tang, rikkunshi-to, interferon, warfarin, salazosulfapyridine, dichloroferamide, fominoben, D-penicillamine, propylthiouracil, corticosteroid, flavoxate, allopurinol, ethoxysclerol and the like

In therapeutic treatment of rheumatoid arthritis, for example, agents that cause pulmonary fibrosis at high frequency such as methotrexate and sodium aurothiomalate are used as disease-modifying antirheumatic drugs. Further, disease-modifying antirheumatic drugs that may cause pulmonary fibrosis at a relatively low frequency, such as actarit, bucillamine, auranofin, salazosulfapyridine, and D-penicillamine are also used. Although these disease-modifying antirheumatic drugs are useful agent in the rheumatoid arthritis treatment system, pulmonary fibrosis caused as a side effect is a factor of restricting use of these drugs. In recent years, methotrexate, in particular, has come to be used as an antirheumatic agent, and onset of pulmonary fibrosis that is also histopathologically called interstitial pneumonia as the side effect of methotrexate becomes a problem in the rheumatoid arthritis treatment system.

Further, in cancer therapy, cychlophosphamide, Taxol, etoposide, cisplatin, vincristine, vinblastine, irinotecan, gefitinib, and bleomycin are useful as anticancer agents. However, because all of these anticancer agents cause pulmonary fibrosis that is also histopathologically called as interstitial pneumonia as a side effect at a high frequency, they have a problem in the therapeutic treatment system. Bleomycin, gefitinib, irinotecan, and cisplatin are used for therapeutic treatment of lung cancer. However, if patients with lung cancer develop pulmonary fibrosis, the condition is most likely for the patients to be fatal. Among these drugs, bleomycin suffers from a problem that it causes pulmonary fibrosis at a high frequency.

Preferred objects of application of the medicament of present invention are drug-induced pulmonary fibroses caused by these drugs.

In present invention, the type 4 PLA₂ inhibitor is not particularly limited so long as the inhibitor has type 4 PLA₂ inhibitory activity. For example, known type 4 PLA₂ inhibitors can be chosen. Examples of the known type 4 PLA₂ inhibitors include the following inhibitors: the compounds described in U.S. Pat. No. 5,462,954, preferably 2-phenyl-4-ethyl-5-[6-(2H-tetrazol-5-yl)-6-methylheptyloxy]phenol, 8-propyl-7-{3-[4-(4-fluorophenyl)-2-ethyl-5-hydroxyphenyloxy]propyloxy}-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid, and 2-{3-[3-([5-ethyl-2-hydroxy(1,1′-biphenyl)-4-yl]oxy)propyloxy]-2-propylphenyloxy}propionic acid; the compounds described in WO99/43654, preferably 4-(1-benzhydryl-6-chloro-1H-indol-3-ylmethyl)-3-methoxybenzoic acid; the compounds described in WO98/33797, preferably N-{4-(biphenyl-2-ylmethyl-isobutylamino)-1-[2-(4-fluorobenzoyl)benzoyl]pyrrolidin-2-ylmethyl}-3-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)phenyl]acrylamide and the like; the compounds described in WO01/30387, preferably N-{1-[2-(2,4-difluorobenzoyl)benzoyl]-4-tritylsulfanylpyrrolidin-2-ylmethyl}-4-(2,4-dioxothiazolidin-5-ylidenemethyl)benzoic acid amide and the like; the compounds described in WO99/15129, preferably 4-{4-[2-(2-[bis(4-chlorophenyl)methoxy]ethylsulfonyl)ethoxy]phenyl}-1,1,1-trifluoro-2-butanone and the like; the compounds described in WO98/05637, preferably 1-{2-[4-(carboxymethyl)phenoxy]ethyl}-3-dodecanoylindole-2-carboxylic acid and the like; the compounds described in Japanese Patent Unexamined Publication (Kokai) No. 2002-80368, preferably 4-methyl-2-oxo-5-(5,6,7,8-tetrahydronaphthalen-2-yl)oxazolidine-3-carboxylic acid (6-methoxytetrahydropyran-2-yl)amide, 4-methyl-2-oxo-5-(4-methylphenyl)thiazolidine-3-carboxylic acid (tetrahydropyran-2-yl)amide and the like; and the type 4 PLA₂ inhibitors selected from the compounds described in WO98/08818, the compounds described in WO99/43651, the compounds described in WO99/43672, the compounds described in WO03/048122, the compounds described in WO95/10508, the compounds described in WO97/05135, the compounds described in Japanese Patent Unexamined Publication No. 7-126166, the compounds described in Japanese Patent Unexamined Publication No. 7-224076, the compounds described in Japanese Patent Unexamined Publication No. 7-224076, the compounds described in Japanese Patent Unexamined Publication No. 2000-119292, the compounds described in Japanese Patent Unexamined Publication No. 2000-109432, the compounds described in Japanese Patent Unexamined Publication No. 7-223997, the compounds described in the U.S. Pat. No. 5,994,398, the compounds described in WO00/27824, the compounds described in Japanese Patent Unexamined Publication No. 2000-38380, the compounds described in WO00/71118, the compounds described in Japanese Patent No. 3107613, the compounds described in WO03/031414, the compounds described in U.S. Pat. No. 5,453,443, and the compounds described in WO02/038575. Examples further include the following known type 4 PLA₂ inhibitors described in references: arachidonyl trifluoromethyl ketone (Street et al., Biochemistry, 1993, vol. 32, p. 5935); methyl arachidonyl fluorophosphate (Kennedy et al., Mediators of Inflammation, 1994, vol. 3, p. 337); β-lactam derivatives (Burke et al., J. Enzyme Inhibition, 1998, vol. 13, p. 195); choline derivatives (Burke et al., J. Biol. Chem., 1999, Vol. 274, p. 18864); 1,3-disubstituted propan-2-one derivatives, especially 4-[3-(4-decyloxyphenyloxy)-2-oxopropyloxy]benzoic acid (Connolly et al., J. Med. Chem., 2002, vol. 45, p. 1348); Surfactin (Kim et al., Biochem. Pharmacol., 1998, vol. 55, p. 975); 1,1,1-trifluorononadeca-10,13,16-trien-2-one and 1,1,1-trifluorononadeca-10,13-dien-2-one (Amandi-Burgermeister et al., Eur. J. Pharmacol., 1997, vol. 326, p. 237); and 2-oxoamide derivatives (Kokotos et al., J. Med. Chem., 2002, vol. 45, p. 2891).

In the present invention, preferred examples of type 4 PLA₂ inhibitor further include the compounds represented by the aforementioned formula (I) and pharmacologically acceptable salts thereof. Various combinations of the compounds represented by the formula (I) and pharmacologically acceptable salts thereof described in the specification can also be arbitrarily chosen.

When a medicament comprising a type 4 PLA₂ inhibitor as an active ingredient is used as a prophylactic and/or therapeutic agent for fibrosis, as for Compound (I) of the present invention, for example, Compound (I) of the present invention or a pharmaceutically acceptable salt thereof, per se, may be used in an effective amount, or the substance may be used after preparation of a pharmaceutical composition in the form of solid, liquid or gel by mixing the substance with a pharmaceutically acceptable carrier. As for the pharmaceutically acceptable carrier, known information and the information about carriers described in this specification can be referred to. As for known type 4 PLA₂ inhibitors, a known type 4 PLA₂ inhibitor or a pharmaceutically acceptable salt thereof, per se, may be used in an effective amount, or as mentioned above, the inhibitors may be used after preparation of a pharmaceutical composition by mixing the inhibitor with a pharmaceutically acceptable carrier.

It would be readily understood by those skilled in the art that progression-preventing agents, that is used for preventing progression of pathological conditions, occasionally fall within the scope of the agent for prophylactic and/or therapeutic treatment of the present invention.

Examples of the dosage form for preparation of the aforementioned pharmaceutical composition, tablet, powder, granule, syrup, suspension, capsule, inhalant, injection, and the like, and in order to prepare the compositions, various carriers are used depending on the type of the composition. Examples of the carrier for oral agents include, for example, excipients, binders, lubricants, flowability improvers, and colorants. When an inhalant is prepared (examples of administration method include a method of inhaling powder of the pharmaceutical composition or a solution obtained by dissolving or suspending the pharmaceutical composition in a solvent, per se, a method of inhaling mist of the composition prepared by using a sprayer called atomizer or nebulizer), the preparation the aforementioned pharmaceutical composition in the form of solid can be referred to for preparation of a powder for the inhalation, and a powder obtained is preferably further made into micropowder. When the composition is inhaled as a liquid, preferred examples of the preparation method include a method of dissolving a solid pharmaceutical composition, which is prepared by referring to the above explanation, in distilled water or a suitable solvent to obtain a solution of medicament upon use, and a method of preparing a liquid pharmaceutical composition prepared by referring the above explanation to obtain a solution of medicament. As for a size of the aforementioned powder or mist of a solution of a medicament to be inhaled, a particle size may be suitable for inhalation. For example, an upper limit is preferably 100 μm or less, further preferably 50 μm or less, most preferably 10 μm or less. A lower limit is not particularly limited, and a smaller particle size is more preferred. When an injection and the like are prepared, distilled water for injection, physiological saline, glucose solution, vegetable oil for injection, propylene glycol, polyethylene glycols and the like can generally be used as diluents. Further, antimicrobial agents, antiseptics, stabilizers, isotonic agents, soothing agents, and the like may be added, as required.

When the aforementioned prophylactic and/or therapeutic agent is administered, a suitable dosage form can be chosen and administered via a suitable route. For example, the agent can be orally administered in the form of a tablet, a powder, a granule, a syrup, a suspension, or a capsule. The agent can also be administered via transairway route in the form of an inhalant. Further, the agent can be administered subcutaneously, intradermally, intravascularly, intramuscularly or intraperitoneally in the form of injection including a drip infusion. Furthermore, the agent can be transmucosally administered in the form of a sublingual agent or a suppository, and can be transdermally administered in the form of a gel, a lotion, an ointment, a cream, or a spray.

A dose thereof varies depending on the dosage form, and the age, weight, degree of symptoms of a patient and the like. Examples of the dose include generally an administration at a dose of 1 to 1,000 mg per day for an adult once to three times a day. Every day administration for a period of several days to two months is commonly applied. The daily dose and the administration period may be increased or decreased depending on symptoms of a patient.

As for the application of the aforementioned prophylactic and/or therapeutic agent, the agent may be administered to patients with pulmonary fibrosis as explained above. In addition, the prophylactic and/or therapeutic agent of the present invention containing a type PLA₂ inhibitor as an active ingredient may preferably be administered after the administration of, most preferably immediately after the administration of an agent, which may possibly induces pulmonary fibrosis as an adverse reaction. Furthermore, as for the administration time, the prophylactic and/or therapeutic agent of the present invention may be administered simultaneously with an agent which may possibly induces pulmonary fibrosis as an adverse reaction, or the agent of the present invention may be administered beforehand.

EXAMPLES

The present invention will be further specifically explained with reference to examples. However, the scope of the present invention is not limited to the following examples. In the examples, for thin layer chromatography (TLC), Precoated Silica Gel 60 F254 (produced by Merck, product number: 5715-1M)) was used. After development with chloroform:methanol (1:0 to 1:1), acetonitrile:acetic acid:water (200:1:1 to 100:4:4) or ethyl acetate:hexane (1:0 to 0:1), spots were observed by UV irradiation (254 nm) or color development with ninhydrine or dinitrophenylhydrazine solution in hydrochloric acid. For drying organic solvent, anhydrous magnesium sulfate or anhydrous sodium sulfate was used. As for column chromatography, the indication of “Quad” means use of Quad 1 preparative chromatography system (produced by Biotage), and one or several columns selected from cartridge columns KP-Sil-12M, 40S and 40M produced by the same manufacturer were used depending on the amount of sample. For flash column chromatography, Silica gel 60N (spherical shape, neutral, 40 to 100 μm, produced by Kanto Chemicals) was used. Preparative thin layer chromatography (hereinafter abbreviated as “PTLC”) was performed by using one or several plates of PLC Plate Silica Gel 60 F254 (20×20 cm, thickness: 2 mm, concentration zone: 4 cm, produced by Merck, product number: 13793-1M) were used depending on the amount of sample.

The indication of “LCMS” means that mass spectrum was measured by liquid chromatography-mass spectrometry (LC-MS). Platform-LC type mass spectrometry apparatus (produced by Micromass) was used as the mass spectrometer, and the measurement was performed by the electrospray ionization (ESI) method. As a liquid chromatography apparatus, an apparatus produced by GILSON was used. As a separation column, Mightysil RP-18 GP 50-4.6 (produced by Kanto Chemicals) was used. Elution was generally performed at a flow rate of 2 ml/minute, and Solution A=water [containing 0.1% (v/v) acetic acid] and Solution B=acetonitrile [containing 0.1% (v/v) acetic acid] were used as solvents.

In the tables mentioned below, data indicated by “LCMS” mean data of liquid chromatography-mass spectrometry spectra. In the columns of “Mass”, data of mass spectrometry were shown (the indication “N.D” means that no molecular ion peak was detected). In the columns of “method”, elution conditions of the liquid chromatography are described. In the columns of “RTime”, retention times in the liquid chromatography are shown. For the indication of retention time in the liquid chromatography, the indication “A” for elution condition means that measurement was performed by elution with a linear gradient of 5 to 100% (v/v) Solution B from 0 minute to 5 minutes and then with 100% Solution B until 6 minutes. Similarly, the indication “B” for elution condition means that measurement was performed by elution with 30% (v/v) Solution B from 0 minute to 0.5 minute, then with a linear gradient of 30 to 95% (v/v) Solution B from 0.5 minute to 4 minutes and then with 95% (v/v) Solution B until 6 minutes. For the compounds with the indication C in the columns of elution conditions, data of mass spectrometry measured by fast atomic bombardment mass spectrometry (FAB-MS) using JEOL-JMS-SX102 (produced by JEOL Co., Ltd.) were mentioned in the columns of “Mass”. Further, for the compounds with the indication D in the elution conditions, an apparatus manufactured by Waters Ltd. was used as a liquid chromatography apparatus. As a column for separation, Develosil C³⁰-UG-5 (50×4.6 mm, Nomura Kagaku Co., Ltd.) was used. Measurement was performed under elution condition with a linear gradient of 5 to 98% (v/v) Solution B from 0 minute to 4 minutes and then with 100% Solution B until 6 minutes.

In the columns indicated as “Exp.”, compound numbers are shown. When the tables include a column indicated as “position”, substituting positions of substituents are indicated in the column. The abbreviations used in the tables have the following meanings.

n: normal, i: iso, s: secondary, t: tertiary, c: cyclo, D: di, Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Pen: pentyl, Hex: hexyl, Hep: heptyl, Ph: phenyl, Bn: benzyl, Py: pyridyl, Indan: indanyl, Ac: acetyl, CHO: formyl, COOH: carboxyl, NO2: nitro, DMA: dimethylamino, NH2: amino, CF3: trifluoromethyl, F: fluoro, Cl: chloro, Br: bromo, OMe: methoxy, OH: hydroxy, TFA: trifluoroacetyl, SO₂: sulfonyl, CO: carbonyl, Nap: naphthyl, Ind: 1H-indolyl, 1HIdz: 1H-indazolyl, 2HIdz: 2H-indazolyl, Bzt: benzothiazole, 2ABzt: 2-aminobenzothiazole, BF: benzofuranyl, BT: benzo[b]thienyl, Qu: Quinolyl, IQ: isoquinolyl

The numbers given before the substituents indicate substituting positions. The numbers given with hyphens before abbreviations of aromatic rings indicate substituting positions of the aromatic rings. (S) indicates optically active substances with S-configuration, and (R) indicates optically active substances with R-configuration. Representative examples of the substituents shown in the tables with abbreviations are listed in Table 2 mentioned below.

TABLE 2 Structure abbreviation

cPenMeO

2EtBuO

cHexO

(R)1PhEtO

2-IndanO

2(3-Py)EtO

5-Ind

1Me-5-1HIdz

2Me-5-Bzt

3-Qu

cHexMeO

2,3DMeBuO

cHepO

2ClBnO

2(4FPh)EtO

2(PhO)EtO

2-Nap

1Me-5-Ind

5-Bzt

5-BT

6-1Q

iBiO

cPenO

BnO

4FBnO

2(4DMAPh)EtO

3F,4(OMe)BnO

1-Nap

5-1HIdz

5-2ABzt

5-BF

The manufacturers of the regents used may sometimes be indicated with the following abbreviations.

TCI: Tokyo Kasei Kogyo Co., Ltd., Ald: Aldrich Co., KANTO: Kanto Kagaku, WAKO: Wako Pure Chemical Industries, Ltd., LANC: Lancaster Synthesis, MAYB: Maybridge, plc. Example A-1 Synthesis of methyl 3-(4-hydroxyphenyl)propionate (Intermediate 1)

A solution obtained beforehand by adding thionyl chloride (18.3 ml, WAKO) dropwise to methanol (250 ml) and mixing the mixture under ice cooling was added dropwise with a solution of 3-(4-hydroxyphenyl)propionic acid (16.6 g, TCI) in methanol (50 ml) under ice cooling, stirred for 30 minutes, warmed to room temperature, and further stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with diethyl ether (200 ml). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 1, 17.95 g).

Synthesis of methyl 3-(4-cyclopentylmethyloxyphenyl)propionate (Intermediate 2)

A solution of cyclopentane methanol (4.05 ml, Ald) in anhydrous tetrahydrofuran (abbreviated as “THF” hereinafter, 40 ml) was added with triethylamine (6.49 ml, WAKO), added dropwise with methanesulfonyl chloride (3.48 ml, WAKO) under ice cooling, and stirred for 30 minutes. The reaction mixture was added with water (50 ml), and extracted with diethyl ether (80 ml×2). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. A solution obtained beforehand by adding 60% sodium hydride (1.15 g, KANTO) to a solution of Intermediate 1 (4.50 g) in N,N-dimethylformamide (abbreviated as “DMF” hereinafter, 35 ml) under ice cooling and stirring the solution for 15 minutes was added with a solution of the aforementioned residue in DMF (10 ml) under ice cooling. The reaction mixture was stirred for 15 minutes, then warmed to room temperature, stirred for 45 minutes, and further stirred at 60° C. for 15 hours. The reaction mixture was added with water (100 ml) and diethyl ether (200 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=9:1) to obtain the title compound (Intermediate 2, 5.58 g).

Synthesis of methyl 3-(3-bromo-4-cyclopentylmethyloxyphenyl)propionate (Compound No. A-1)

A solution of Intermediate 2 (1.31 g) in acetonitrile (50 ml) was added with N-bromosuccinimide (hereinafter abbreviated as “NBS”, 979 mg, KANTO), stirred at room temperature for 2 hours, then warmed to 40° C., and stirred for 3 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (200 ml) and washed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. A-1, 1.69 g).

Example A-2 Synthesis of 3-(3-bromo-4-methoxyphenyl)propionic acid (Intermediate 3)

According to the procedure described in the synthesis method of Compound No. A-1 provided that the reaction was carried out under ice cooling for 30 minutes and at room temperature for 3 hours, 3-(4-methoxyphenyl)propionic acid (27.0 g, TCI) and NBS (29.4 g) were reacted and treated to obtain the title compound (Intermediate 3, 38.1 g).

Synthesis of 3-(3-bromo-4-hydroxyphenyl)propionic acid (Intermediate 4)

According to a procedure described in a literature (Carreno, M. C., J. Org. Chem., 1995, vol. 60, p. 5328), a 1 M solution of boron tribromide in methylene chloride (200 ml, Fluka) was added dropwise with a solution of Intermediate 4 (23.5 g) in methylene chloride (200 ml) at −78° C., warmed to room temperature after 30 minutes, and further stirred for 1.5 hours. The reaction mixture was poured into ice water (750 ml), and stirred at room temperature for 1 hour. The reaction mixture was added with diethyl ether (750 ml)) for extraction. The organic layer was added with 2 N aqueous sodium hydroxide (250 ml×2) for extraction, and then the aqueous layer was made acidic with 5 N aqueous hydrochloric acid under ice cooling, and extracted with diethyl ether (375 ml×2) again. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 4, 23.5 g).

Synthesis of methyl 3-(3-bromo-4-hydroxyphenyl)propionate (Intermediate 5)

According to the procedure described in the synthesis method of Intermediate 1 provided that the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1), Intermediate 4 (21.15 g) and thionyl chloride (15.0 ml) were reacted and treated in methanol to obtain the title compound (Intermediate 5, 20.36 g).

Synthesis of methyl (3-bromo-4-cyclohexylmethyloxyphenyl)propionate (Compound No. A-2)

A solution of Intermediate 5 (1.29 g) in DMF (25 ml) was added with potassium carbonate (0.86 g) and bromomethylcyclohexane (1.05 ml, TCI), stirred under argon atmosphere at room temperature for 2 hours, then warmed to 60° C., and stirred for 17 hours. The reaction mixture was poured into ice water, and extracted with isopropyl ether (200 ml). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=9:1) to obtain the title compound (Compound No. A-2, 1.45 g).

Example A-5 Synthesis of methyl 3-(3-bromo-4-cyclopentyloxyphenyl)propionate (Compound No. A-5)

A solution of Intermediate 5 (4.50 g) in DMF (20 ml) was added with 60% sodium hydride (440 mg, KANTO) under ice cooling. The reaction mixture was stirred for 10 minutes, then added with bromocyclopentane (1.61 ml, TCI), warmed to room temperature, stirred for 1.5 hours, then warmed to 60° C., and further stirred for 16 hours. The reaction mixture was added with water (50 ml) and isopropyl ether (300 ml)) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether 7:1) to obtain the title compound (Compound No. A-5, 2.50 g).

Example A-6 Synthesis of methyl 3-(3-bromo-4-cyclohexyloxyphenyl)propionate (Compound No. A-6)

A solution of Intermediate 5 (2.06 g), triphenylphosphine (hereinafter abbreviated as “Ph₃P”, 6.28 g, WAKO) and cyclohexanol (2.53 ml, WAKO) in anhydrous THF (60 ml) was added dropwise with a 40% solution of diisopropylazodicarboxylic acid ester in toluene (hereinafter abbreviated as “40% DLAD”, 11.35 ml, WAKO) under ice cooling over 10 minutes. The reaction mixture was stirred for 10 minutes, then warmed to room temperature, and stirred for 18.5 hours. The reaction mixture was added with water (50 ml) and ethyl acetate (200 ml)) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:isopropyl ether=8:1) to obtain the title compound (Compound No. A-6, 2.35 g).

Example A-20 Synthesis of methyl 3-(3 bromo-5-chloro-4-hydroxyphenyl)propionate (Intermediate 6)

A solution of Intermediate 5 (516 mg) in chloroform (5 ml) was added with sulfuryl chloride (177 μl), and stirred at room temperature for 21 hours. The reaction mixture was poured into aqueous saturated sodium hydrogencarbonate (20 ml), and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 6, 290 mg).

Synthesis of methyl 3-(3-bromo-5-chloro-4-cyclopentylmethyloxyphenyl)propionate (Compound No. A-20)

According to the procedure described in the synthesis method of Compound No. A-6 provided that the purification was performed by column chromatography (Quad, hexane:ethyl acetate=30:1), Intermediate 6 (278 mg), Ph₃P (747 mg), cyclopentane methanol (308 μl), and 40% DIAD (1.34 ml) were reacted and treated to obtain the title compound (Compound No. A-20, 337 mg).

Example A-21 Synthesis of ethyl 3-(3-fluoro-4-methyloxyphenyl)acrylate (Intermediate 7)

A solution of 3-fluoro-4-methoxybenzaldehyde (2.20 g, Ald) in 1,2-diethoxyethane (5 ml) was added with ethyl diethylphosphonoacetate (3.12 ml, TCI) and added with 60% sodium hydride (624 mg) under ice cooling. After being stirred for 10 minutes, the reaction mixture was warmed to room temperature, and stirred for 5 hours. The reaction mixture was added with ethyl acetate (90 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 7, 3.16 g).

Synthesis of ethyl 3-(3-fluoro-4-methoxyphenyl)propionate (Intermediate 8)

A solution of Intermediate 7 (3.01 g) in ethyl acetate (50 ml) and methanol (25 ml) was added with 10% palladium/carbon (300 mg, Merck), and stirred at room temperature for 2 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 8, 3.02 g).

Synthesis of 3-(3-fluoro-4-methoxyphenyl)propionic acid (Intermediate 9)

A solution of Intermediate 8 (2.97 g) in methanol (40.0 ml) was added with 2 N aqueous sodium hydroxide (15.0 ml) and stirred at 60° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, then made acidic with aqueous 5% hydrochloric acid under ice cooling, and extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 9, 2.40 g).

Synthesis of 3-(3-fluoro-4-hydroxyphenyl)propionic acid (Intermediate 10)

A pyridine/hydrochloric acid complex prepared by mixing pyridine (30 ml) and concentrated hydrochloric acid (30 ml) and heating the mixture at 190° C. for 1 hour was added with Intermediate 9 (2.40 g) and stirred at 190° C. for 1.5 hours. The reaction mixture was poured into 1 N hydrochloric acid (100 ml) cooled with ice, and extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 10, 1.98 g).

Synthesis of methyl 3-(3-fluoro-4-hydroxyphenyl)propionate (Intermediate 11)

According to the procedure described in the synthesis method of Intermediate 1, Intermediate 10 (1.77 g) and thionyl chloride (1.65 ml) were reacted and treated in methanol to obtain the title compound (Intermediate 11, 1.85 g).

Synthesis of methyl 3-(3-bromo-5-fluoro-4-hydroxyphenyl)propionate (Intermediate 12)

According to the procedure described in the synthesis method of Compound No. A-1 with the modifications that the reaction was carried out for 2 hours under ice cooling, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), Intermediate 11 (1.84 g) and NBS (1.74 g) were reacted and treated to obtain the title compound (Intermediate 12, 1.74 g).

Synthesis of methyl 3-(3-bromo-4-cyclopentylmethyloxy-5-fluorophenyl)propionate (Compound No. A-21)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 22 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=50:1), Intermediate 11 (310 mg), tributylphosphine (hereinafter abbreviated as “^(n)Bu₃P”, 405 μl, WAKO) instead of Ph₃P, cyclopentane methanol (176 μl), and N,N,N′,N′-tetramethylazodicarboxamide (hereinafter abbreviated as “TMAD”, 279 mg, TCI) instead of 40% DIAD were reacted and treated to obtain the title compound (Compound No. A-21, 386 mg).

Example A-24 Synthesis of 4-cyclopentyloxy-3-methylbenzaldehyde (Intermediate 13)

According to the procedure described in the synthesis method of Compound No. A-2 with the modifications that the reaction was carried out for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=9:1), 4-hydroxy-3-methylbenzaldehyde (283 mg, TCI), potassium carbonate (578 mg) and bromocyclopentane (430 μl) were reacted and treated to obtain the title compound (Intermediate 13, 350 mg).

Synthesis of ethyl 3-(4-cyclopentyl-3-methylphenyl)acrylate (Intermediate 14)

According to the procedure described in the synthesis method of Intermediate 7 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate==9:1), Intermediate 13 (342 mg), ethyl diethylphosphonoacetate (408 μl) and 60% sodium hydride (82 mg) were reacted and treated to obtain the title compound (Intermediate 14, 450 mg).

Synthesis of ethyl 3-(4-cyclopentyl-3-methylphenyl)propionate (Intermediate 15)

According to the procedure described in the synthesis method of Intermediate 8, Intermediate 14 (446 mg) and 10% palladium/carbon (20 mg) were reacted and treated under hydrogen gas atmosphere to obtain the title compound (Intermediate 15, 439 mg).

Synthesis of ethyl 3-(3-bromo-4-cyclopentyl-5-methylphenyl)propionate (Compound No. A-24)

According to the procedure described in the synthesis method of Compound No. A-1, Intermediate 15 (437 mg) and NBS (320 mg) were reacted and treated to obtain the title compound (Compound No. A-24, 545 mg).

Example A-251 Synthesis of 3-bromo-4-(t-butyldimethylsilyloxy)-5-methoxybenzaldehyde (Intermediate 16)

A solution of 3-bromovanillin (1.16 g, TCI) in anhydrous DMF (20 ml) was added with imidazole (408 mg, TCI), added dropwise with a solution of 4-(N,N-dimethylamino)pyridine (25 mg) and t-butyldimethylsilyl chloride (904 mg, TCI) in DMF (15 ml) under ice cooling, stirred 30 minutes, then warmed to room temperature, and further stirred 3 hours. The reaction mixture was added with water (100 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (Intermediate 16, 1.75 g).

Synthesis of ethyl 3-[3-bromo-4-(t-butyldimethylsilyloxy)-5-methoxyphenyl]acrylate (Intermediate 17)

According to the procedure described in the synthesis method of Intermediate 7 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=9:1), Intermediate 16 (910 mg), ethyl diethylphosphonoacetate (530 μl) and 60% sodium hydride (120 mg) were reacted and treated to obtain the title compound (Intermediate 17, 937 mg).

Synthesis of ethyl 3-[3-bromo-4-(t-butyldimethylsilyloxy)-5-methoxyphenyl]propionate (Intermediate 18)

According to the procedure described in the synthesis method of Intermediate 8, Intermediate 17 (945 mg) and 10% palladium/carbon (95 mg) were reacted and treated under hydrogen gas atmosphere to obtain the title compound (Intermediate 18, 760 mg).

Synthesis of ethyl 3-(3-bromo-4-hydroxy-5-methoxyphenyl)propionate (Intermediate 19)

A solution of Intermediate 18 (750 mg) in THF (50 ml) was added with a 1 M solution of tetrabutylammonium fluoride in THF (5 ml, TCI), and stirred for 1.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (30 ml), and extracted with ethyl acetate (50 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate 19, 542 mg).

Synthesis of ethyl 3-(3-bromo-4-cyclopentyloxy-5-methoxyphenyl)propionate (Compound No. A-25)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=7:1), Intermediate 19 (400 mg), Ph₃P (1.31 g), cyclopentanol (4501 μl), and TMAD (860 mg) were reacted and treated to obtain the title compound (Compound No. A-25, 376 mg).

Example A-26 Synthesis of methyl 3-(3-bromo-4-cyclopentylmethyloxy-5-nitrophenyl)propionate (Compound No. A-26)

A solution obtained beforehand by adding 70% nitric acid (3.9 ml) to acetic anhydride (30 ml) under ice cooling and stirring the mixture for 10 minutes was added with a solution of Compound No. A-1 (5.12 g) in acetonitrile (25 ml) at −15° C. over 15 minutes, and stirred further for 15 minutes. The reaction mixture was poured into 1 N aqueous sodium hydroxide (500 ml) containing ice, and extracted with diethyl ether (300 ml×2). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Compound No. A-26, 3.68 g).

Example A-31 Synthesis of methyl 3-(3-bromo-4-phenoxyphenyl)propionate (Compound No. A-31)

A solution of Intermediate 5 (3.08 g) in anhydrous N-methylpyrrolidone (9.5 ml, WAKO) was successively added with cesium carbonate (3.58 g, WAKO), iodobenzene (1.4 ml, TCI), dipivaloylmethane (0.12 ml, TCI) and copper(I) chloride (275 mg, WAKO), and stirred 120° C. for 16 hours under argon gas atmosphere. The reaction mixture was added with t-butyl methyl ether (25 ml), and insoluble solids were removed by filtration. The filtrate was washed successively with 2 N aqueous hydrochloric acid and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=1:10) to obtain the title compound (Compound No. A-31, 1.00 g).

Example B-96 Synthesis of methyl 3-(3-bromo-4-methoxyphenyl)propionate (Intermediate 20)

According to the procedure described in the synthesis method of Intermediate 1 provided that the purification was performed by flash column chromatography (hexane:ethyl acetate=6:1), Intermediate 3 (1.60 g) and thionyl chloride (1.44 ml) were reacted and treated in methanol to obtain the title compound (Intermediate 20, 1.63 g).

Synthesis of methyl 3-(3-bromo-4-methoxy-5-nitrophenyl)propionate (Intermediate 21)

A solution of Intermediate 20 (3.20 g) in acetic anhydride (25 ml) was added with potassium nitrate (1.30 g) under ice cooling and stirred for 10 minutes, and the solution was added dropwise with concentrated sulfuric acid (730 μl) over 10 minutes. The reaction mixture was stirred for 10 minutes for 10 minutes at the same temperature, then warmed to room temperature, and further stirred for 30 minutes. The reaction mixture was poured into 1 N aqueous sodium hydroxide (250 ml) containing ice, and extracted with isopropyl ether (200 ml×2). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 21, 2.73 g).

Synthesis of 3-(3-bromo-4-methoxy-5-nitrophenyl)propionic acid (Intermediate 22)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1 hour, Intermediate 21 (12.73 g) and 2 N aqueous sodium hydroxide (40 ml) were reacted and treated to obtain the title compound (Intermediate 22, 11.53 g).

Synthesis of 3-(3-bromo-4-hydroxy-5-nitrophenyl)propionic acid (Intermediate 23)

According to the procedure described in the synthesis method of Intermediate 4 provided that the reaction was carried out for 2 hours, Intermediate 22 (11.53 g) and a 1 M solution of boron tribromide in methylene chloride (100 ml) were reacted and treated to obtain the title compound (Intermediate 23, 10.68 g).

Synthesis of methyl 3-(3-bromo-4-hydroxy-5-nitrophenyl)propionate (Intermediate 24)

According to the procedure described in the synthesis method of Intermediate 1 provided that the reaction was carried out for 17.5 hours, Intermediate 23 (10.68 g) and thionyl chloride (8.06 ml) were reacted and treated to obtain the title compound (Intermediate 24, 8.27 g).

Synthesis of methyl 3-[3-bromo-4-(indan-2-yloxy)-5-nitrophenyl]propionate (Compound No. B-96)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=19:1), Intermediate 24 (151 mg), Ph₃P (260 mg), 2-hydroxyindane (133 mg, TCI) and 40% DIAD (470 μl) were reacted and treated to obtain the title compound (Compound No. B-96, 192 mg).

Example B-99 Synthesis of methyl 3-(3-amino-5-bromo-4-cyclopentyloxyphenyl)propionate (Compound No. B-99)

A solution of Compound No. A-28 (416 mg) in a mixture of THF (5 ml) and methanol (5 ml) was added with Raney 2800 nickel (230 mg, Ald) and stirred at room temperature for 6 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 5:2) to obtain the title compound (Compound No. B-99, 143 mg).

Example B-103 Synthesis of methyl 3-[4-benzyloxy-5-bromo-3-(2,2,2-trifluoroacetylamino)phenyl]propionate (Compound No. B-103)

A solution of Compound No. B-100 (58.7 mg) in methylene chloride (2 ml) was added with triethylamine (76 μl), added dropwise trifluoroacetic anhydride (91 μl, TCI) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 2 hours. The reaction mixture was added with water (5 ml), and extracted with methylene chloride (20 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=3:1) to obtain the title compound (Compound No. B-103, 59.1 mg).

Example B-105 Synthesis of methyl 3-[4-benzyloxy-5-bromo-3-(N-methylamino)phenyl]propionate (Compound No. B-105)

A solution of Compound No. B-100 (105 mg) in DMF (3 ml) was added with 60% sodium hydride (20 mg) under ice cooling, and stirred for 10 minutes. This reaction mixture was added dropwise with methyl iodide (32 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 2 hours. The reaction mixture was poured into water, and added with ethyl acetate (30 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. B-105, 17 mg).

Example B-109 Synthesis of 3-[4-benzyloxy-5-bromo-3-(N,N-dimethylamino)phenyl]propionic acid (Compound No. B-109)

A solution of Compound No. B-100 (105 mg) in DMF (3 ml) was added with 60% sodium hydride (40 mg) under ice cooling, and stirred for 10 minutes. This reaction mixture was added dropwise with methyl iodide (300 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 16 hours. The reaction mixture was poured into water, and added with ethyl acetate (30 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. B-109, 88 mg).

Examples B-113 and B-114 Syntheses of 3-(3-bromo-4-cyclopentyloxy-5-hydroxyphenyl)propionic acid (Compound No. B-113) and 3-(5-acetoxy-3-bromo-4-cyclopentyloxyphenyl)propionic acid (Compound No. B-114)

A solution of Compound No. B-99 (415 mg) in acetic acid (1.5 ml) was added with 20% sulfuric acid (1.0 ml). This reaction mixture was added dropwise with an aqueous solution (0.5 ml) of sodium nitrite (78 mg) over 10 minutes, while the temperature of the reaction mixture was maintained below 10° C., and further stirred for 5 minutes. This reaction mixture was added dropwise to a solution of sodium acetate (348 mg) in acetic acid (3.5 ml) heated and stirred at 100° C. beforehand over 5 minutes, and further stirred for 10 minutes with heating. The reaction solution was poured into ice water (50 ml), and extracted with isopropyl ether (100 ml×2). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compounds (Compound No. B-113, 47 mg and Compound No. B-114, 105 mg).

Example B-117 Synthesis of methyl 3-(3,5-dibromo-4-cyclopentylmethyloxyphenyl)propionate (Compound No. B-117)

A solution of Intermediate 1 (670 mg) in acetonitrile (30 ml) was added with NBS (990 mg), stirred at room temperature for 2 hours, then warmed to 40° C., and stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (100 ml), and washed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 18 hours under ice cooling, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), the residue was reacted with Ph₃P (1460 mg), cyclopentane methanol (560 mg) and 40% DIAD (2.6 ml) and treated to obtain the title compound (Compound No. B-117, 710 mg).

Examples A-1 to A-33

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-A-1. The compounds were prepared according to the preparation methods of the compound numbers (e.g., “A-1”) or the intermediate numbers (e.g., “Int 2”) shown in the columns of “Syn” in the tables. “Int” means an intermediate compound number. When the preparation required a plurality of steps, a plurality of compound numbers or intermediate compound numbers are mentioned in the columns of “Syn”. For example, an indication of “Int 2, A-1” in a column of “Syn” means that “the compound is prepared from a compound prepared according to the procedure described in the synthesis method of Intermediate 2 according to the procedure described in the synthesis method of Compound No. A-1.” When the compounds were synthesized according to the procedure described in the synthesis method of Compound No. A-6, TMAD or di-t-butyl azodicarboxylate (hereinafter abbreviated as “DBAB”) was sometimes used instead of 40% DIAD.

TABLE A-1

LCMS Exp. Rx′O Y′ Zx′ G Syn method RTime Mass A-1 cPenMeO Me H Br A-1 C 341 (M⁺ + 1) A-2 cHexMeO Me H Br A-2 C 354 (M⁺) A-3 iBuO Me H Br A-2 A 5.34 N.D A-4 2EtBuO Me H Br A-2 A-5 cPenO Me H Br A-5 C 326 (M⁺) A-6 cHexO Me H Br A-6 C 340 (M⁺) A-7 cHepO Me H Br A-6 A-8 BnO Me H Br A-2 A-9 1PhEtO Me H Br A-2 A-10 2FBnO Me H Br A-2 A-11 4FBnO Me H Br A-2 A-12 2ClBnO Me H Br A-2 A-13 4ClBnO Me H Br A-2 A 4.85 N.D A-14 4MeBnO Me H Br A-2 A-15 4CF3BnO Me H Br A-2 A-16 2(4DMAPh)EtO Me H Br A-6 A-17 2(PhO)EtO Me H Br A-6 A 5.04 N.D A-18 1(2FPh)EtO Me H Br A-6 A-19 1(4ClPh)EtO Me H Br A-6 A 4.82 N.D A-20 cPenMeO Me Cl Br A-20 C 375 (M⁺ + 1) A-21 cPenMeO Me F Br A-21 A-22 cPenO Me F Br A-21 C 345 (M⁺ + 1) A-23 cHexO Me F Br A-21 A-24 cPenO Et Me Br A-24 A 5.82 N.D A-25 cPenO Et OMe Br A-25 A-26 cPenMeO Me NO2 Br A-26 C 340 (M⁺ + 1) A-27 cHexMeO Me NO2 Br A-26 A-28 cPenO Me NO2 Br A-26 C 372 (M⁺ + 1) A-29 cHexO Me NO2 Br A-26 A-30 2-IndanO Me NO2 Br A-26 A 5.03 N.D A-31 PhO Me H Br A-31 A 5.15 N.D A-32 4ClPhO Me H Br A-31 A 5.47 N.D A-33 4MeOPhO Me H Br A-31 A 5.02 N.D

Examples B-1 to B-119

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-B-1 to Table B-3.

TABLE B-1

LCMS Exp. Rx′O Y′ Zx′ G Syn method RTime Mass B-1 nPrO Me H Br A-2 C 279 (M⁺) B-2 iPrO Me H Br A-2 B-3 sBuO Me H Br A-6 B-4 iPenO Me H Br A-6 B-5 1,3DMeBuO Me H Br A-6 B-6 2MeBuO Me H Br A-6 B-7

Me H Br A-6 B-8

Me H Br A-6 B-9 2,3DMeBuO Me H Br A-6 B-10 cPenO Me H Cl A-6 C 361 (M⁺ + 1) B-11 trans2Me, Me H Br A-6 cPenO B-12 3Me, Me H Br A-6 cPenO B-13 trans2Me, Me H Br A-6 cHexO B-14 cis2Me, Me H Br A-6 cHexO B-15 3Me, Me H Br A-6 C 354 (M⁺ + 1) cHexO B-16 4Me, Me H Br A-6 cHexO B-17 2,3DMe, Me H Br A-6 cHexO B-18 3,4DMe, Me H Br A-6 C 368 (M⁺ + 1) cHexO B-19 3,5DMe, Me H Br A-6 cHexO B-20

Me H Br A-6 B-21

Me H Br A-6 B-22

Me H Br A-6 B-23 1PhPrO Me H Br A-6 B-24 (S)1PhPrO Me H Br A-6 B-25 BenzhydrylO Me H Br A-6 B-26

Me H Br A-6 C 391 (M⁺ + 1) B-27

Me H Br A-6 B-28 2Ph,1MeEtO Me H Br A-6 B-29 2Ph,2MeEtO Me H Br A-6 B-30 2(2FPh), Me H Br A-6 1MeEtO B-31 2(3CF₃Ph), Me H Br A-6 1MeEtO B-32 3PhBuO Me H Br A-6 B-33 5OMe-2-IndanO Me H Br A-6 B-34 5,6D(OMe)-2- Me H Br A-6 IndanO B-35 5F-2-IndaneO Me H Br A-6 B-36 1-IndaneO Me H Br A-6 B-37

Me H Br A-6 B-38

Me H Br A-6 B-39 3FBnO Me H Br A-6 B-40 2MeBnO Me H Br A-6 C 363 (M⁺ + 1) B-41 3MeBnO Me H Br A-6 B-42 3,5DMeBnO Me H Br A-6 B-43 4tBuBnO Me H Br A-6 B-44 2CF₃BnO Me H Br A-6 B-45 4CF₃BnO Me H Br A-6 B-46 3(CF₃O)BnO Me H Br A-6 B-47 4(CF₃O)BnO Me H Br A-6 B-48 4(nBuO)BnO Me H Br A-6 B-49

Me H Br A-6 C 406 (M⁺ + 1) B-50 3,4DFBnO Me H Br A-6 B-51 2,4DFBnO Me H Br A-6 B-52 4Br,2FBnO Me H Br A-6 B-53 2,4DClBnO Me H Br A-6 B-54 3,4DClBnO Me H Br A-6 B-55 2,3DClBnO Me H Br A-6 B-56 2,6DClBnO Me H Br A-6 B-57 3,5DClBnO Me H Br A-6 B-58 2-NapMeO Me H Br A-6 C 399 (M⁺ + 1) B-59 1-NapMeO Me H Br A-6 B-60

Me H Br A-6 B-61

Me H Br A-6 B-62

Me H Br A-6 C 339 (M⁺ + 1) B-63 2PhBnO Me H Br A-6 B-64 4PhBnO Me H Br A-6 B-65 2PhEtO Me H Br A-6 B-66 2(2MePh)EtO Me H Br A-6 B-67 2(3MePh)EtO Me H Br A-6 B-68 2(4MePh)EtO Me H Br A-6 B-69 2(3FPh)EtO Me H Br A-6 B-70 2(3ClPh)EtO Me H Br A-6 B-71 2(2CF₃Ph)EtO Me H Br A-6 B-72 2(4CF₃Ph)EtO Me H Br A-6 B-73 2(2OMePh)EtO Me H Br A-6 B-74 2(2-Nap)EtO Me H Br A-6 C 413 (M⁺ + 1) B-75 2(3-Ind)EtO Me H Br A-6 B-76

Me H Br A-6 B-77 2(PhO)EtO Me H Br A-6 B-78 2(2ClPhO)EtO Me H Br A-6 B-79 2(4ClPhO)EtO Me H Br A-6 B-80

Me H Br A-6 C 407 (M⁺ + 1) B-81

Me H Br A-6 B-82

Me H Br A-6 B-83

Me H Br A-6 B-84 2(PhS)EtO Me H Br A-6 C 379 (M⁺ + 1) B-85 2-BztO Me H Br A-6 B-86 (6OMe-2-Bzt)O Me H Br A-6 B-87 cPenO Me Cl Br A-20 B-88 1(4FPh)EtO Me Cl Br A-20 B-89 1PhEtO Me F Br A-21 B-90 1(4FPh)EtO Me F Br A-21 B-91 1PhEtO Et Me Br A-24 B-92 1(4FPh)EtO Et Me Br A-24 B-93 1PhEtO Me OMe Br A-25 B-94 1(4FPh)EtO Me OMe Br A-25 B-95 BnO Me NO2 Br A-26 B-96 2-IndanO Me NO2 Br A-26 A 4.44 N.D B-97 5OMe-2-IndanO Me NO2 Br A-26 B-98 4CF3BnO Me NO2 Br A-26 B-99 cPenO Me NH2 Br B-99 C 342 (M⁺ + 1) B-100 BnO Me NH2 Br B-99 B-101 1PhEtO Me NH2 Br B-99 B-102 5OMe-2-IndanO Me NH2 Br B-99 B-103 BnO Me NHTFA Br B-103 B-104 cPenO Me NHTFA Br B-103 C 438 (M⁺ + 1) B-105 BnO Me NHMe Br B-105 B-106 cPenO Me NHMe Br B-105 C 356 (M⁺ + 1) B-107 1PhEtO Me NHMe Br B-105 B-108 1(4FPh)EtO Me NHMe Br B-105 B-109 BnO Me NMe2 Br B-109 B-110 cPenO Me NMe2 Br B-109 C 370 (M⁺ + 1) B-111 1PhEtO Me NMe2 Br B-109 B-112 1(4FPh)EtO Me NMe2 Br B-109 B-113 cPenO Me OH Br B-113 C 343 (M⁺ + 1) B-114 cPenO Me OCO Br B-114 Me B-115 1(4FPh)EtO Me OH Br B-113 B-116 1(4FPh)EtO Me OCO Br B-114 Me B-117 cPenMeO Me Br Br B-117 B-118 cPenO Me Br Br B-117 A 5.98 N.D B-119 1(4FPh)EtO Me Br Br B-117

Example C-1 Synthesis of 3-bromo-4-cyclohexylmethyloxybenzaldehyde (Intermediate 25)

According to the procedure described in the synthesis method of Compound No. A-2 provided that the purification was performed by flash column chromatography (hexane:isopropyl ether=5:1), 3-bromo-4-hydroxybenzaldehyde (17.4 g), potassium carbonate (23.9 g) and bromomethylcyclohexane (36.2 ml) were reacted and treated to obtain the title compound (Intermediate 25, 18.7 g).

Synthesis of 4-cyclohexylmethyloxy-3-(naphthalen-2-yl)benzaldehyde (Compound No. C-1)

A solution of 2-naphthaleneboronic acid (535 mg) in methanol (5.0 ml), Intermediate 25 (1.16 g), and 2 M aqueous sodium carbonate (0.9 ml) were added with toluene (10.0 ml) and tetrakistriphenylphosphinepalladium(0) [hereinafter abbreviated as “(Ph₃P)₄Pd”] (116 mg, Nakarai Tecs), and stirred at 80° C. for 17 hours. The reaction mixture was added with ethyl acetate (100 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=10:1) to obtain the title compound (Compound No. C-1, 345 mg).

Example D-10 Synthesis of 3-bromo-4-hydroxy-5-nitrobenzaldehyde (Intermediate 26)

A solution of 3-bromo-4-hydroxybenzaldehyde (6.30 g) in acetic acid (45 ml) was added dropwise with 70% nitric acid (5.85 ml) on a water bath, then added with sodium nitrite (62 mg), and further stirred for 2 hours. The reaction mixture was poured into ice water (300 ml), and precipitates were taken by filtration, and washed with water (50 ml×3). The precipitates were dried under reduced pressure for 24 hours to obtain the title compound (Intermediate 26, 5.88 g).

Synthesis of 3-bromo-4-cyclohexylmethyloxy-5-nitrobenzaldehyde (Intermediate 27)

According to the procedure described in the synthesis method of Compound No. A-2 provided that the purification was performed by flash column chromatography (hexane:ethyl acetate=7:1), Intermediate 26 (5.5 g), potassium carbonate (3.94 g) and bromomethylcyclohexane (3.94 ml) were reacted and treated to obtain the title compound (Intermediate 27, 5.2 g).

Synthesis of 4-cyclohexylmethyloxy-3-(naphthalen-2-yl)-5-nitrobenzaldehyde (Compound No. D-10)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 15 hours at 80° C., and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=7:1), Intermediate 27 (2.65 g), 2-naphthaleneboronic acid (3.01 g), 2 M aqueous sodium carbonate (7.5 ml) and (Ph₃P)₄Pd (960 mg) were reacted and treated to obtain the title compound (Compound No. D-10, 2.96 g).

Examples C-1 to C-8

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-C-1.

TABLE C-1

Rx′O Zx′ AR′ LCMS Exp. Rx′O Position Zx′ Position AR′ Position Syn method RTime Mass C-1 cHexMeO 4 H — 2-Nap 5 C-1 C-2 cHexMeO 4 H — 1-Nap 5 C-1 C-3 cHexMeO 4 H — 2OMe-6-Nap 5 C-1 C 374 (M⁺) C-4 cHexMeO 4 H — 5-Ind 5 C-1 C-5 cPenMeO 4 H — 2-Nap 5 C-1 C-6 cPenMeO 4 H — 5-Ind 5 C-1 C-7 cPenO 4 H — 2-Nap 5 C-1 C 316 (M⁺) C-8 cPenO 4 H — 5-Ind 5 C-1 C 305 (M⁺)

Examples D-1 to D-29

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-D-1

TABLE D-1

Rx′O Zx′ AR′ LCMS Exp. Rx′O Position Zx′ Position AR′ Position Syn method RTime Mass D-1 cHexMeO 4 H — 2-BT 3 C-1 C 350 (M⁺) D-2 cHexMeO 4 H — 2-BF 3 C-1 D-3 cHexMeO 4 H — 1Me-5-Ind 3 C-1 C 316(M⁺) D-4 cHexMeO 4 H — 5-1HIdz 3 C-1 D-5 cHexMeO 4 H — 1Me-5-1HIdz 3 C-1 D-6 2(2FPh)EtO 4 H — 2-Nap 3 C-1 D-7 2(2FPh)EtO 4 H — 5-Ind 3 C-1 D-8 2-IndanO 4 H — 5-Ind 3 C-1 D-9 2-IndanO 4 H — 5-1HIdz 3 C-1 D-10 cPenMeO 4 NO2 5 2-Nap 3 D-10 C 330 (M⁺ + 1) D-11 cPenMeO 4 NO2 5 5-Ind 3 D-10 D-12 cHexMeO 4 NO2 5 2-Nap 3 D-10 D-13 cHexMeO 4 NO2 5 2-BF 3 D-10 D-14 cPenO 4 NO2 5 2-Nap 3 D-10 D-15 cPenO 4 NO2 5 5-Ind 3 D-10 C 350(M⁺) D-16 2(2FPh)EtO 4 NO2 5 2-Nap 3 D-10 D-17 2(2FPh)EtO 4 NO2 5 5-Ind 3 D-10 D-18 2-IndanO 4 NO2 5 5-Ind 3 D-10 D-19 2-IndanO 4 NO2 5 1Me-5-1HIdz 3 D-10 A 3.85 414 (M⁺ + 1) D-20 cPenO 2 H — 2-Nap 5 C-1 C 316(M⁺) D-21 cPenO 2 H — 5-Ind 5 C-1 C 305(M⁺) D-22 cPenO 3 H — 2-Nap 5 C-1 D-23 cPenO 3 H — 5-Ind 5 C-1 D-24 cPenO 5 H — 2-Nap 2 C-1 D-25 cPenO 5 H — 5-Ind 2 C-1 D-26 cPenO 4 H — 2Nap 2 C-1 D-27 cPenO 4 H — 5-Ind 2 C-1 D-28 cPenO 3 H — 2-Nap 2 C-1 D-29 cPenO 3 H — 5-Ind 2 C-1

Example E-1 Synthesis of 5-bromo-2-cyclopentylmethyloxypyridine (Intermediate 28)

A solution of potassium t butoxide (550.6 mg, WAKO) in dehydrated THF (10 ml) was added with cyclopentane methanol (450 μl), and then added with a solution of 2,5-dibromopyridine (982.8 mg, TCI) in dehydrated THF (15 ml) under ice cooling. The reaction mixture was stirred for 30 minutes, then warmed to room temperature, and stirred for 11 hours. The reaction mixture was added with water (100 ml) and ethyl acetate (60 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine sequentially, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=15:1) to obtain the title compound (Intermediate 28, 896 mg).

Synthesis of 2-cyclopentylmethyloxypyridine-5-carbaldehyde (Intermediate 29)

A solution of Intermediate 28 (895 mg) in anhydrous THF (10 ml) was added dropwise with a 1.6 M solution of n-butyllithium in hexane (2.70 ml, Ald) over 5 minutes with cooling at −78° C. under argon gas atmosphere, and stirred for 20 minutes. This reaction mixture was added with dehydrated DMF (330 μl, WAKO) over 3 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was added with water (10 ml), and extracted with ethyl acetate (30 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 29, 1.04 g).

Synthesis of ethyl 3-(2-cyclopentylmethyloxypyridin-5-yl)acrylate (Intermediate 30)

According to the procedure described in the synthesis method of Intermediate 7 with the modification that the reaction was carried out for 1 hour, Intermediate 29 (450 mg), ethyl diethylphosphonoacetate (530/1) and 60% sodium hydride (120 mg) were reacted and treated to obtain the title compound (Intermediate 30, 394 mg).

Synthesis of ethyl 3-(2-cyclopentylmethyloxypyridine-5-yl)propionate (Intermediate 31)

According to the procedure described in the synthesis method of Intermediate 8 with the modifications that the reaction was carried out for 1 hour, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=15:1), Intermediate 30 (392 mg) and 10% palladium/carbon (30 mg) were reacted and treated to obtain the title compound (Intermediate 31, 246 mg).

Synthesis of ethyl 3-(3-bromo-2-cyclopentylmethyloxypyridin-5-yl)propionate (Compound No. E-1)

A solution of Intermediate 31 (5.20 g) in acetonitrile (50 ml) was warmed to 35° C., added dropwise with bromine (1.1 ml, WAKO), then added with NBS (3.72 g), and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (200 ml), and washed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Compound No. E-1, 6.51 g).

Example E-7 Synthesis of 2-benzyloxy-5-bromopyridine (Intermediate 32)

According to the procedure described in the synthesis method of Intermediate 28 provided that the reaction was carried out for 1 hour, potassium t-butoxide (3.13 g), benzyl alcohol (3.10 ml) and 2,5-dibromopyridine (4.79 g) were reacted and treated to obtain the title compound (Intermediate 32, 5.36 g).

Synthesis of 2-benzyloxypyridine-5-carbaldehyde (Intermediate 33)

According to the procedure described in the synthesis method of Intermediate 29, Intermediate 32 (5.10 g), a 1.6M solution of n-butyllithium in hexane (15.5 ml) and dehydrated DMF (1.9 ml) were reacted and treated to obtain the title compound (Intermediate 33, 2.75 g).

Synthesis of ethyl 3-(2-benzyloxypyridin-5-yl)acrylate (Intermediate 34)

According to the procedure described in the synthesis method of Intermediate 7, Intermediate 33 (2.74 g), ethyl diethylphosphonoacetate (3.12 ml) and 60% sodium hydride (635 mg) were reacted and treated to obtain the title compound (Intermediate 34, 2.12 g).

Synthesis of ethyl 3-(2-hydroxypyridin-5-yl)propionate (Intermediate 35)

According to the procedure described in the synthesis method of Intermediate 8 provided that the reaction was carried out for 2.5 hours, Intermediate 54 (2.12 g) and 10% palladium/carbon (120 mg) were reacted and treated to obtain the title compound (Intermediate 35, 1.26 g).

Synthesis of ethyl 3-(3-bromo-2-hydroxypyridin-5-yl)propionate (Intermediate 36)

According to the procedure described in the synthesis method of Compound No. E-1 with the modifications that the reaction was carried out for 2.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=1:2), Intermediate 35 (1.23 g), bromine (340 μl) and NBS (1.19 g) were reacted and treated to obtain the title compound (Compound No. 36, 1.42 g).

Synthesis of ethyl 3-[5-bromo-6-[(S)-1-phenylethyloxy]pyridin-3-yl]propionate (Compound No. E-7)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 11 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Intermediate 36 (137 mg), Ph₃P (273 mg), (R)-1-phenylethanol (150 μl, TCI) and 40% DIAD (400 μl) were reacted and treated to obtain the title compound (Compound No. E-7, 167 mg).

Example E-13 Synthesis of ethyl 3-(5-bromo-6-(4-trifluoromethylbenzyloxy)pyridin-3-yl)propionate (Compound No. E-13)

A solution of Intermediate 36 (71.5 mg) in chloroform (7 ml) was added with 4-trifluoromethylbenzyl bromide (109.2 mg, TCI) and silver carbonate (120 mg, WAKO), and stirred at room temperature for 11 hours under light shielding. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. E-13, 114 mg).

Example E-1 to 16

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-E-1.

TABLE E-1

LCMS Exp. Rx′O Y′ G Syn method RTime Mass E-1 cPenMeO Et Br E-1 A 5.98 356(M⁺) E-2 cHexMeO Et Br E-1 E-3 iBuO Et Br E-1 A 5.57 N.D E-4 2EtBuO Et Br E-1 E-5 cPenO Et Br E-1 A 5.62 342 (M⁺) E-6 cHexO Et Br E-1 E-7 (R)1PhEtO Et Br E-7 A 5.60 N.D E-8 2(4DMAPh)EtO Et Br E-7 E-9 2(2FPh)EtO Et Br E-7 E-10 2(3FPh)EtO Et Br E-7 E-11 2(4ClPh)EtO Et Br E-7 E-12 2(PhO)EtO Et Br E-7 E-13 4CF₃BnO Et Br E-13 A 5.78 432 (M⁺) E-14 2MeBnO Et Br E-13 E-15 2ClBnO Et Br E-13 E-16 1(4FPh)EtO Et Br E-7

Example F-1 Synthesis of 4-(3-bromo-4-methoxyphenyl)butyric acid (Intermediate 37)

According to the procedure described in the synthesis method of Compound No. A-1 provided that the reaction was carried out under ice cooling for 30 minutes and for 20 hours at room temperature, 4-(4-methoxyphenyl)butyric acid (11.64 g, Ald) and NBS (11.21 g) were reacted and treated to obtain the title compound (Intermediate 37, 16.30 g).

Synthesis of methyl 4-(3-bromo-4-hydroxyphenyl)butyrate (Intermediate 38)

According to the procedure described in the synthesis method of Intermediate 4, Intermediate 37 (12.51 g) and a 1 M solution of boron tribromide in methylene chloride (100 ml) were reacted and treated, and the obtained residue was reacted with thionyl chloride (8.4 ml) in methanol and treated according to the procedure described in the synthesis method of Intermediate 1 to obtain the title compound (Intermediate 38, 10.48 g).

Synthesis of methyl 4-(3-bromo-4-cyclopentylmethyloxyphenyl)butyrate (Compound No. F-1)

According to the procedure described in the synthesis method of Compound No. A-6 provided that the purification was performed by column chromatography (Quad, hexane:isopropyl alcohol=10:1), Intermediate 38 (2.72 g), Ph₃P (7.86 g), cyclopentane methanol (3.24 ml) and 40% DIAD (14.2 ml) were reacted and treated to obtain the title compound (Compound No. F-1, 3.33 g).

Examples F-1 to F-4

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-F-1.

TABLE F-1

LCMS meth- Exp. Rx′O Y′ Zx′ G n Syn od RTime Mass F-1 cPenMeO Me H Br 3 F-1 C 354(M⁺) F-2 cPenO Me H Br 3 F-1 F-3 cHexO Me H Br 3 F-1 C 354(M⁺) F-4 1(4FPh) Me H Br 3 F-1 EtO

Example G-1 Synthesis of methyl 3-[4-methoxy-3-(naphthalen-2-yl)phenyl]propionate (Intermediate 39)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by flash column chromatography (hexane:isopropyl ether=8:1), Intermediate 20 (460 mg), 2-naphthaleneboronic acid (886 mg), 2 M aqueous sodium carbonate (1.6 ml) and (Ph₃P)₄Pd (298 mg) were reacted and treated to obtain the title compound (Intermediate 39, 580 mg).

Synthesis of 3-[4-methoxy-3-(naphthalen-2-yl)phenyl]propionic acid (Intermediate 40)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Intermediate 39 (773 mg) and 2 N aqueous sodium hydroxide (2.3 ml) were reacted and treated to obtain the title compound (Intermediate 40, 674 mg).

Synthesis of methyl 3-[4-hydroxy-3-(naphthalen-2-yl)phenyl]propionate (Intermediate 41)

According to the procedure described in the synthesis method of Intermediate 10, pyridine (5 ml), concentrated hydrochloric acid (5 ml), and Intermediate 40 (551 mg) were reacted and treated to obtain crude powder substance. This substance was reacted with thionyl chloride (282 μl) in methanol and treated according to the procedure described in the synthesis method of Intermediate 1 to obtain the title compound (Intermediate 41, 531 mg).

Synthesis of methyl 3-[4-cyclopentyloxy-3-(naphthalen-2-yl)phenyl]propionate (Compound No. G-1).

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by flash column chromatography (hexane:isopropyl ether=6:1), Intermediate 41 (100 mg), Ph₃P (262 mg), cyclopentanol (91 μl, TCI) and 40% DIAD (473 μl) were reacted and treated to obtain the title compound (Compound No. G-1, 120 mg).

Example G-2 Synthesis of 3-[4-cyclopentyloxy-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. G-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 4 hours, Compound No. G-1 (115 mg), and 2 N aqueous sodium hydroxide (0.75 ml) were reacted and treated to obtain the title compound (Compound No. G-2, 108 mg).

Example G-3 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)phenyl]propionate (Compound No. G-3)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 3 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1), Compound No. A-6 (833 mg), 5-indoleboronic acid (657 mg), 2 M aqueous sodium carbonate (2.4 ml) and (Ph₃P)₄Pd (233 mg) were reacted and treated to obtain the title compound (Compound No. G-3, 900 mg).

Example G-4 Synthesis of 3-[4-cyclopentyloxy-3-(1H-indole-5-yl)phenyl]propionic acid (Compound No. G-4)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. G-3 (144 mg) and 2 N aqueous sodium hydroxide (420 μl) were reacted and treated to obtain the title compound (Compound No. G-4, 127 mg).

Example G-9 Synthesis of methyl 3-[4-benzyloxy-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate (Compound No. G-9)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 6 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Compound No. A-8 (349 mg), 1-methyl-1H-indazole-5-boronic acid (283 mg), 2 M aqueous sodium carbonate (0.9 ml) and (Ph₃P)₄Pd (94.3 mg) were reacted and treated to obtain the title compound (Compound No. G-9, 370 mg).

Example G-10 Synthesis of 3-[4-benzyloxy-5-(1-methyl-1H-indazol-5-yl)phenyl]propionic acid (Compound No. G-10)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 4 hours, Compound No. G-9 (80 mg) and 2 N aqueous sodium hydroxide (0.20 ml) were reacted and treated to obtain the title compound (Compound No. G-10, 71 mg).

Synthesis of methyl 3-[4-hydroxy-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate (Intermediate 42)

A solution of Compound No. G-9 (314 mg) in a mixture of ethyl acetate (3 ml) and methanol (3 ml) was added with 10% palladium/carbon (12 mg), and stirred at room temperature for 16 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 48, 288 mg).

Example G-23 Synthesis of methyl 3-(3-bromo-4-t-butyldimethylsilyloxyphenyl)propionate (Intermediate 43)

According to the procedure described in the synthesis method of Intermediate 16 provided that the reaction was carried out for 16 hours, Intermediate 5 (5.18 g), imidazole (2.04 g) and t-butyldimethylsilyl chloride (4.52 g) were reacted and treated to obtain the title compound (Intermediate 43, 8.42 g).

Synthesis of methyl 3-[4-(t-butyldimethylsilyloxy-3-(1H-indol-5-yl)phenyl)propionate (Intermediate 44)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that reaction was performed for 12.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=9:1), 5-indoleboronic acid (4.83 g), Intermediate 34 (7.46 g), 2 M aqueous sodium carbonate (18 ml) and (Ph₃P)₄Pd (1.62 g) were reacted and treated to obtain the title compound (Intermediate 44, 5.04 g).

Synthesis of methyl 3-[4-hydroxy-3-(1H-indol-5-yl)phenyl]propionate (Intermediate 45)

According to the procedure described in the synthesis method of Intermediate 19 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=3:1), Intermediate 35 (5.04 g), acetic acid (2.8 ml) and a 1 M solution of tetrabutylammonium fluoride in THF (49 ml, TCI) were reacted and treated to obtain the title compound (Intermediate 45, 3.13 g).

Synthesis of methyl 3-[3-(1H-indol-5-yl)-4-(4-methylphenylmethyloxy)phenyl]-propionate (Compound No. G-23)

According to the procedure described in the synthesis method of Compound No. A-2 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 45 (80 mg), potassium carbonate (114 mg) and 4-methylbenzyl bromide (54 μl, TCI) were reacted and treated to obtain the title compound (Compound No. G-23, 104 mg).

Example G-24 Synthesis of 3-[3-(1H-indol-5-yl)-4-(4-methylphenylmethyloxy)phenyl]propionic acid (Compound No. G-24)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. G-23 (99 mg) and 2 N aqueous sodium hydroxide (500 μl) were reacted and treated to obtain the title compound (Compound No. G-24, 84 mg).

Example G-106 Synthesis of N-[2-(t-butyldiphenylsilyloxy)ethyl]aniline (Intermediate 46)

A solution of 2-anilinoethanol (5.82 g, TCI) in anhydrous DMF (50 ml) was added with imidazole (3.23 g, TCI), added dropwise with a solution of t-butyldiphenylsilyl chloride (12.48 g, TCI) in DMF (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 3.5 hours. The reaction mixture was added with water (100 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed successively with water and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (Intermediate 46, 15.61 g).

Synthesis of N-benzyl-N-[2-(t-butyldiphenylsilyloxy)ethyl]aniline (Intermediate 47)

According to the procedure described in the synthesis method of Compound No. A-2 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 46 (15.60 g), potassium carbonate (8.91 g) and benzyl bromide (6.05 ml, TCI) were reacted and treated to obtain the title compound (Intermediate 47, 19.23 g).

Synthesis of 2-(N-benzyl-N-phenylamino)ethanol (Intermediate 48)

According to the procedure described in the synthesis method of Intermediate 9 with the modifications that the reaction was carried out for 1 hour, and the purification was performed by flash column chromatography (hexane:ethyl acetate=5:1), Intermediate 47 (19.22 g) and a 1 M solution of tetrabutylammonium fluoride in THF (86 ml) were reacted and treated to obtain the title compound (Intermediate 48, 9.06 g).

Synthesis of methyl 3-{4-[2-(N-benzyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. G-106)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=7:1), Intermediate 41 (1.26 g), Ph₃P (1.34 g), Intermediate 48 (1.01 g) and DBAB (1.18 g) instead of 40% DIAD were reacted and treated to obtain the title compound (Compound No. G-106, 1.39 g).

Example G-107 Synthesis of methyl 3-{3-(naphthalen-2-yl)-4-[2-(N-phenylamino)ethyloxy]phenyl}propionate (Compound No. G-107)

A solution of Compound No. G-106 (1.39 g) in a mixture of THF (10 ml) and methanol (20 ml) was added with concentrated hydrochloric acid (75 μl, WAKO) and 10% palladium/carbon (142 mg), and stirred at room temperature for 3 hours under hydrogen gas atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Compound No. G-107, 842 mg).

Example G-108 Synthesis of 3-{3-(naphthalen-2-yl)-4-[2-(phenylamino)ethyloxy]phenyl}propionic acid (Compound No. G-108)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. G-107 (46 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. G-108, 41 mg).

Examples G-1 to G-121

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-G-1 to Table-G-4.

TABLE G-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass G-1 cPenMeO Me H 2-Nap G-1 C 388(M⁺) G-2 cPenMeO H H 2-Nap G-2 C 375 (M⁺ + 1) G-3 cPenMeO Me H 5-Ind G-3 G-4 cPenMeO H H 5-Ind G-4 C 363 (M⁺) G-5 cPenMeO Me H 1Me-5-Ind G-3 G-6 cPenMeO H H 1Me-5-Ind G-4 A 391 (M⁺ + 1) G-7 cPenMeO Me H 5-1HIdz G-3 G-8 cPenMeO H H 5-1HIdz G-4 G-9 BnO Me H 1Me-5-1HIdz G-9 G-10 BnO H H 1Me-5-1HIdz G-10 G-11 cPenMeO Me H 1Me-5-1HIdz G-3 G-12 cPenMeO H H 1Me-5-1HIdz G-4 G-13 2EtBuO H H 2-Nap G-1,G-2 A 377 (M⁺ + 1) G-14 2EtBuO H H 5-Ind G-3,G-4 G-15 4Me,cHexO H H 2-Nap G-1,G-2 G-16 4Me,cHexO H H 5-Ind G-3,G-4 D 5.46 378 (M⁺ + 1) G-17

H H 2-Nap G-1,G-2 G-18

H H 5-Ind G-3,G-4 G-19 cHepO H H 5-Ind G-3,G-4 G-20 3PhPrO H H 2-Nap G-1,G-2 G-21 4PhBuO H H 5-Ind G-3,G-4 G-22

H H 2-Nap G-1,G-2 D 5.40 414 (M⁺ + 1) G-23 4MeBnO Me H 5-Ind G-23 G-24 4MeBnO H H 5-Ind G-24 G-25 2(4MePh)EtO H H 2-Nap G-1,G-2 G-26 2(4MePh)EtO H H 5-Ind G-1,G-2 G-27 4ClBnO H H 2-Nap G-23,G-24 G-28 4CF₃BnO H H 5-Ind G-23,G-24 G-29 3F,4(OMe)BnO H H 2-Nap G-1,G-2 G-30 3F,4(OMe)BnO H H 5-Ind G-1,G-2 G-31

H H 2-Nap G-1,G-2 G-32

H H 5-Ind G-1,G-2 G-33

H H 2-Nap G-1,G-2 G-34

H H 5-Ind G-1,G-2 G-35

H H 2-Nap G-1,G-2 G-36

H H 5-Ind G-1,G-2 G-37 1IndanO H H 5-Ind G-1,G-2 D 5.19 398 (M⁺ + 1) G-38 2IndanO H H 2-Nap G-1,G-2 G-39 2lndanO H H 5-Ind G-1,G-2 G-40 5OMe-2-IndanO H H 2-Nap G-1,G-2 C 439(M⁺ + 1) G-41 5,6D(OMe)-2-IndanO H H 5-Ind G-1,G-2 C 458(M⁺ + 1) G-42 5F-2-IndanO H H 2-Nap G-1,G-2 G-43 5F-2-IndanO H H 5-Ind G-1,G-2 C 416(M⁺ + 1) G-44

H H 2-Nap G-1,G-2 G-45

H H 5-Ind G-1,G-2 A 5.46 412 (M⁺ + 1) G-46

H H 2-Nap G-1,G-2 G-47

H H 5-1HInd G-1,G-2 G-48 2(2MePh)EtO H H 2-Nap G-1,G-2 G-49 2(2MePh)EtO H H 5-Ind G-1,G-2 G-50 2(3FPh)EtO H H 2-Nap G-1,G-2 G-51 2(2ClPh)EtO H H 2-Nap G-1,G-2 G-52 2(3ClPh)EtO H H 5-Ind G-1,G-2 G-53 2(2CF₃Ph)EtO H H 5-Ind G-1,G-2 G-54 4(CF₃Ph)EtO H H 2-Nap G-1,G-2 G-55 2(2OMePh)EtO H H 2-Nap G-1,G-2 C 427 (M⁺ + 1) G-56 2(4OMePh)EtO H H 5-Ind G-1,G-2 G-57 2(1-NapEt)O H H 2-Nap G-1,G-2 G-58 2(2-Nap)EtO H H 2-Nap G-1,G-2 G-59 2(2-Nap)EtO H H 5-Ind G-1,G-2 C 435 (M⁺) G-60 2(4ClPh)EtO H H 2-Nap G-1,G-2 G-61

H H 5-Ind G-1,G-2 D 5.11 430 (M⁺ + 1) G-62

H H 1Me-5-1HIdz G-1,G-2 G-63 2(PhS)EtO H H 2-Nap G-1,G-2 A 402 (M⁺ + 1) G-64 2(PhS)EtO H H 5-Ind G-1,G-2 G-65 3PhPrO H H 5-Ind G-1,G-2 G-66 2ClBnO H H 2-Nap G-1,G-2 G-67 2BrBnO H H 5-Ind G-1,G-2 C 450 (M⁺) G-68 3,5DMeBnO H H 5-Ind G-1,G-2 G-69 4tBuBnO H H 2-Nap G-1,G-2 G-70 2CF₃BnO H H 2-Nap G-1,G-2 G-71 4CF₃BnO H H 5-Ind G-1,G-2 G-72 4nBuBnO H H 5-Ind G-1,G-2 G-73 3.5DClBnO H H 2-Nap G-1,G-2 G-74 2,3DClBnO H H 5-Ind G-1,G-2 G-75 2PhBnO H H 2-Nap G-1,G-2 G-76 4PhBnO H H 5-Ind G-1,G-2 A 448 (M⁺ + 1) G-77

H H 2-Nap G-1,G-2 G-78

H H 5-Ind G-1,G-2 G-79

H H 2-Nap G-1,G-2 G-80

H H 5-Ind G-1,G-2 G-81

H H 2-Nap G-1,G-2 C 386 CM⁺ + 1) G-82

H H 5-Ind G-1,G-2 G-83

H H 2-Nap G-1,G-2 G-84

H H 5-Ind G-1,G-2 G-85

H H 2-Nap G-1,G-2 G-86

H H 5-Ind G-1,G-2 G-87

H H 2-Nap G-1,G-2 G-88

H H 5-Ind G-1,G-2 G-89

H H 2-Nap G-1,G-2 G-90

H H 5-Ind G-1,G-2 G-91

H H 2-Nap G-1,G-2 G-92

H H 5-Ind G-1,G-2 G-93

H H 2-Nap G-1,G-2 G-94

H H 2-Nap G-1,G-2 C 384 (M⁺ + 1) G-95

H H 5-Ind G-1,G-2 G-96

H H 2-Nap G-1,G-2 G-97

H H 5-Ind G-1,G-2 G-98

H H 2-Nap G-1,G-2 G-99

H H 5-Ind G-1,G-2 G-100

H H 2-Nap G-1,G-2 G-101

H H 5-Ind G-1,G-2 C 423 (M⁺ + 1) G-102

H H 2-Nap G-1,G-2 G-103

H H 5-Ind G-1,G-2 G-104

H H 2-Nap G-1,G-2 G-105

H H 5-Ind G-1,G-2 G-106 2(Ph,BnN)EtO Me H 2-Nap G-106 G-107 2(PhNH)EtO Me H 2-Nap G-107 G-108 2(PhNH)EtO H H 2-Nap G-108 C 412(M⁺ + 1) G-109 2(PhNH)EtO Me H 5-Ind G-107 G-110 2(PhNH)EtO H H 5-Ind G-108 G-111 2(PhNH)EtO Me H 1Me-5-Ind G-107 G-112 2(PhNH)EtO H H 1Me-5-Ind G-108 C 415(M⁺ + 1) G-113 2(PhNH)EtO Me H 5-1HIdz G-107 G-114 2(PhNH)EtO H H 5-1HIdz G-108 G-115 2(PhNH)EtO Me H 1Me-5-1HIdz G-107 A 4.76 430(M⁺ + 1) G-116 2(PhNH)EtO H H 1Me-5-1HIdz G-108 C 416(M⁺ + 1) G-117 iBuO H H 1Me-5-Ind G-1,G-2 C 352(M⁺ + 1) G-118 iBuO H H 1Me-5-1HIdz G-1,G-2 C 353(M⁺ + 1) G-119 PhO H H 1Me-5-1HIdz G-3,G-4 A 4.10 373(M⁺ + 1) G-120 4ClPhO H H 1Me-5-1HIdz G-3,G-4 A 4.46 407(M⁺ + 1) G-121 4MeOPhO H H 1Me-5-1HIdz G-3,G-4 A 4.12 403(M⁺ + 1)

Examples H-1 to H-32

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-H-1 and Table-H-2.

TABLE H-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass H-1

Me H 2-Nap G-1 H-2

H H 2-Nap G-2 H-3

Me H 5-Ind G-1 C 375 (M⁺ + 1) H-4

H H 5-Ind G-2 H-5

Me H 1Me-5-Ind G-1 H-6

H H 1Me-5-Ind G-2 H-7

Me H 5-1HIdz G-1 H-8

H H 5-1HIdz G-2 H-9

Me H 1Me-5-1HIdz G-1 H-10

H H 1Me-5-1HIdz G-2 C 454 (M⁺ + 1) H-11

H H 2-Nap G-1,G-2 H-12

H H 1Me-5-Ind G-1,G-2 C 452 (M⁺ + 1) H-13

H H 2-Nap G-1,G-2 H-14

H H 1Me-5-Ind G-1,G-2 H-15

H H 2-Nap G-1,G-2 C 464 (M⁺ + 1) H-16

H H 1Me-5-Ind G-1,G-2 H-17

H H 2-Nap G-1,G-2 C 450 (M⁺ + 1) H-18

H H 1Me-5-Ind G-1,G-2 H-19

H H 2-Nap G-1,G-2 H-20

H H 1Me-5-Ind G-1,G-2 H-21

H H 2-Nap G-1,G-2 H-22

H H 1Me-5-Ind G-1,G-2 C 471 (M⁺ + 1) H-23

H H 2-Nap G-1,G-2 H-24

H H 1Me-5-Ind G-1,G-2 H-25

H H 2-Nap G-1,G-2 H-26

H H 1Me-5-Ind G-1,G-2 H-27

H H 2-Nap G-1,G-2 H-28

H H 1Me-5-Ind G-1,G-2 C 460 (M⁺ + 1) H-29

H H 2-Nap G-1,G-2 H-30

H H 1Me-5-Ind G-1,G-2 H-31

H H 2-Nap G-1,G-2 C 452 (M⁺ + 1) H-32

H H 1Me-5-Ind G-1,G-2

Example J-1 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-fluoro-5-(1H-indol-5-yl)phenyl]propionate (Compound No. J-1)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), Compound No. A-21 (154 mg), 5-indoleboronic acid (100 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph₃P)₄Pd (50 mg) were reacted and treated to obtain the title compound (Compound No. J-1, 125 mg).

Example J-2 Synthesis of 3-[4-cyclopentylmethyloxy-3-fluoro-5-(1H-indol-5-yl)phenyl]propionic acid (Compound No. J-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. J-1 (124 mg) and 2 N aqueous sodium hydroxide (630 μl) were reacted and treated to obtain the title compound (Compound No. J-2, 97 mg)

Example J-3 Synthesis of methyl 3-[3-chloro-4-cyclopentylmethyloxy-5-(1H-indol-5-yl)phenyl]propionate (Compound No. J-3)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), Compound No. A-20 (151 mg), 5-indoleboronic acid (97 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph₃P)₄Pd (46 mg) were reacted and treated to obtain the title compound (Compound No. J-3, 160 mg).

Example J-4 Synthesis of 3-[3-chloro-4-cyclopentylmethyloxy-5-(1H-indol-5-yl)phenyl]propionic acid (Compound No. J-4)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. J-3 (135 mg) and 2 N aqueous sodium hydroxide (660 μl) were reacted and treated to obtain the title compound (Compound No. J-4, 97 mg).

Examples J-1 to J-92

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-J-1 to Table-J-3

TABLE J-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass J-1 cPenMeO Me F 5-Ind J-1 A 396 (M⁺ + 1) J-2 cPenMeO H F 5-Ind J-2 J-3 cPenMeO Me Cl 5-Ind J-3 J-4 cPenMeO H Cl 5-Ind J-4 C 398 (M⁺ + 1) J-5 cPenMeO Me F 2-Nap J-1 J-6 cPenMeO H F 2-Nap J-2 J-7 cPenMeO Me F 1Me-5-Ind J-1 J-8 cPenMeO H F 1Me-5-Ind J-2 J-9 cPenMeO Me F 5-1HIdz J-1 J-10 cPenMeO H F 5-1HIdz J-2 J-11 cPenMeO Me F 1Me-5-1HIdz J-1 J-12 cPenMeO H F 1Me-5-1HIdz J-2 C 397 (M⁺ + 1) J-13 2EtBuO H F 2-Nap G-1,G-2 J-14 2EtBuO H F 5-Ind G-1,G-2 J-15 4Me,cHexO H F 2-Nap G-1,G-2 J-16 4Me,cHexO H F 1Me-5-Ind G-1,G-2 J-17

H F 2-Nap G-1,G-2 J-18

H F 1Me-5-Ind G-1,G-2 C 452 (M⁺ + 1) J-19 cHepO H F 2-Nap G-1,G-2 J-20 3PhPrO H F 1Me-5-Ind G-1,G-2 J-21 4PhBuO H F 2-Nap G-1,G-2 J-22

H F 1Me-5-Ind G-1,G-2 J-23 1(4MePh)EtO H F 2-Nap G-1,G-2 J-24 4ClBnO H F 1Me-5-Ind G-1,G-2 J-25 4CF3BnO H F 2-Nap G-1,G-2 J-26 3F,4(OMe)BnO H F 1Me-5-Ind G-1,G-2 J-27

H F 2-Nap G-1,G-2 C 429 (M⁺ + 1) J-28

H F 1Me-5-Ind G-1,G-2 J-29

H F 1Me-5-Ind G-1,G-2 J-30

H F 2-Nap G-1,G-2 J-31

H F 2-Nap G-1,G-2 J-32 1-IndanO H F 2-Nap G-1,G-2 J-33 2-IndaneO H F 1Me-5-Ind G-1,G-2 J-34 2-IndaneO H F 2-Nap G-1,G-2 J-35 5OMe-2-IndanO H F 1Me-5-Ind G-1,G-2 J-36 5,6D(OMe)-2-IndanO H F 2-Nap G-1,G-2 J-37 5F-2-IndanO H F 2-Nap G-1,G-2 J-38 5F-2-IndanO H F 1Me-5-Ind G-1,G-2 J-39

H F 2-Nap G-1,G-2 C 441 (M⁺ + 1) J-40

H F 1Me-5-Ind G-1,G-2 J-41 2(3MePh)EtO H F 2-Nap G-1,G-2 J-42 2(4MePh)EtO H F 1Me-5-Ind G-1,G-2 J-43 2(2ClPh)EtO H F 1Me-5-Ind G-1,G-2 J-44 2(3ClPh)EtO H F 2-Nap G-1,G-2 J-45 2(2CF₃Ph)EtO H F 2-Nap G-1,G-2 J-46 2(2OMePh)EtO H F 1Me-5-Ind G-1,G-2 J-47 2(4OMePh)EtO H F 2-Nap G-1,G-2 J-48 2(2-Nap)EtO H F 1Me-5-Ind G-1,G-2 J-49

H F 2-Nap G-1,G-2 C 458 (M⁺ + 1) J-50

H F 1Me-5-1HIdz G-1,G-2 J-51 2(PhS)EtO H F 1Me-5-Ind G-1,G-2 J-52 3PhPrO H F 2-Nap G-1,G-2 J-53 2ClBnO H F 1Me-5-Ind G-1,G-2 J-54 2BrBnO H F 2-Nap G-1,G-2 J-55 3,5DMeBnO H F 2-Nap G-1,G-2 J-56 4tBuBnO H F 1Me-5-Ind G-1,G-2 C 460 (M⁺ + 1) J-57 2CF₃BnO H F 1Me-5-Ind G-1,G-2 J-58 4CF₃BnO H F 2-Nap G-1,G-2 J-59 4nBuOBnO H F 2-Nap G-1,G-2 J-60 3,5DClBnO H F 1Me-5-Ind G-1,G-2 J-61 2,3DClBnO H F 2-Nap G-1,G-2 J-62 2-NapMeO H F 2-Nap G-1,G-2 C 451 (M⁺ + 1) J-63 1-NapMeO H F 1Me-5-Ind G-1,G-2 J-64 2PhBnO H F 1Me-5-Ind G-1,G-2 J-65 4PhBnO H F 1Me-5-Ind G-1,G-2 J-66 5OMe-2-IndanO H F 2-Nap G-1,G-2 J-67 5OMe-2-IndanO H F 1Me-5-Ind G-1,G-2 J-68 5,6D(OMe)-2-IndanO H F 2-Nap G-1,G-2 J-69 5,6D(OMe)-2-IndanO H F 1Me-5-Ind G-1,G-2 J-70 5F-2-IndanO H F 2-Nap G-1,G-2 J-71 5F-2-IndanO H F 1Me-5-Ind G-1,G-2 J-72

H F 1Me-5-Ind G-1,G-2 J-73

H F 2-Nap G-1,G-2 C 481 (M⁺ + 1) J-74

H F 1Me-5-Ind G-1,G-2 J-75

H F 2-Nap G-1,G-2 J-76

H F 1Me-5-Ind G-1,G-2 J-77

H F 1Me-5-1HIdz G-1,G-2 C 410 (M⁺ + 1) J-78

H F 1Me-5-Ind G-1,G-2 J-79

H F 2-Nap G-1,G-2 J-80

H F 1Me-5-Ind G-1,G-2 J-81

H F 2-Nap G-1,G-2 J-82

H F 1Me-5-Ind G-1,G-2 J-83

H F 1Me-5-Ind G-1,G-2 J-84

H F 1Me-5-Ind G-1,G-2 J-85

H F 1Me-5-Ind G-1,G-2 C 419 (M⁺ + 1) J-86

H F 1Me-5-Ind G-1,G-2 J-87

H F 2-Nap G-1,G-2 J-88

H F 1Me-5-Ind G-1,G-2 J-89

H F 2-Nap G-1,G-2 C 436 (M⁺ + 1) J-90

H F 1Me-5-Ind G-1,G-2 J-91

H F 2-Nap G-1,G-2 J-92

H F 1Me-5-Ind G-1,G-2

Example K-11 Synthesis of methyl 3-[3-bromo-4-cyclopentylmethyloxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. K-11)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=9:1), Compound No. B-117 (306 mg), 2-naphthaleneboronic acid (163 mg), 2 M aqueous sodium carbonate (689 μl) and (Ph₃P)₄Pd (74.2 mg) were reacted and treated to obtain the title compound (Compound No. K-11, 261 mg).

Synthesis of 3-[3-bromo-4-cyclopentylmethyloxy-5-(1H-indol-5-yl)phenyl]propionic acid (Compound No. K-12)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. K-11 (131 mg) and 2 N aqueous sodium hydroxide (400 μl) were reacted and treated to obtain the title compound (Compound No. K-12, 109 mg).

Example K-13 Synthesis of methyl 3-[3-bromo-4-cyclopentylmethyloxy-5-(1H-indol-5-yl)phenyl]propionate (Compound No. K-13)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Compound No. B-117 (102 mg), 5-indoleboronic acid (97 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph₃P)₄Pd (46 mg) were reacted and treated to obtain the title compound (Compound No. K-13, 85 mg).

Example K-14 Synthesis of 3-[3-bromo-4-cyclopentylmethyloxy-5-(1H-indol-5-yl)phenyl]propionic acid (Compound No. K-14)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. K-13 (85 mg) and 2 N aqueous sodium hydroxide (200 μl) were reacted and treated to obtain the title compound (Compound No. K-14, 79 mg).

Example K-17 Synthesis of methyl 3-[3-bromo-4-cyclopentyloxy-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate (Compound No. K-17)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 14 hours at 80° C., and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Compound No. B-118 (306 mg), 1-methyl-1H-indazole-5-boronic acid (175 mg), 2 M aqueous sodium carbonate (0.68 ml) and (Ph₃P)₄Pd (70.1 mg) were reacted and treated to obtain the title compound (Compound No. K-17, 148 mg).

Examples K-1 to K-40

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-K-1 and Table-K-2.

TABLE K-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass K-1

Me F 2-Nap G-1 K-2

H F 2-Nap G-2 K-3

Me F 5-Ind G-1 K-4

H F 5-Ind G-2 C 457(M⁺ + 1) K-5

Me F 1Me-5-Ind G-1 K-6

H F 1Me-5-Ind G-2 C 471(M⁺ + 1) K-7

Me F 5-1HIdz G-1 K-8

H F 5-1HIdz G-2 K-9

Me F 1Me-5-1HIdz G-1 K-10

H F 1Me-5-1HIdz G-2 K-11 cPenMeO Me Br 2-Nap K-11 K-12 cPenMeO H Br 2-Nap K-12 K-13 cPenMeO Me Br 2-Nap K-13 K-14 cPenMeO H Br 5-Ind Int50, C 456(M⁺) K-13 K-15 cPenO H Br 2-Nap K-11, K-12 K-16 cPenO H Br 1Me-5-Ind K-11, K-12 K-17 cPenO Me Br 1Me-5-1HIdz K-11, K-12 K-18 cPenO H Br 1Me-5-1HIdz K-11, A 4.78 443(M⁺) K-12 K-19

H F 2-Nap G-1,G-2 K-20

H F 1Me-5-Ind G-1,G-2 K-21

H F 2-Nap G-1,G-2 K-22

H F 1Me-5-Ind G-1,G-2 K-23

H F 2-Nap G-1,G-2 K-24

H F 1Me-5-Ind G-1,G-2 C 485(M⁺ + 1) K-25

H F 2-Nap G-1,G-2 K-26

H F 1Me-5-Ind G-1,G-2 K-27

H F 2-Nap G-1,G-2 K-28

H F 1Me-5-Ind G-1,G-2 K-29

H F 2-Nap G-1,G-2 K-30

H F 1Me-5-Ind G-1,G-2 K-31

H F 2-Nap G-1,G-2 C 486(M⁺ + 1) K-32

H F 1Me-5-Ind G-1,G-2 K-33

H F 2-Nap G-1,G-2 K-34

H F 1Me-5-Ind G-1,G-2 C 511(M⁺ + 1) K-35

H F 2-Nap G-1,G-2 K-36

H F 1Me-5-Ind G-1,G-2 K-37

H F 2-Nap G-1,G-2 K-38

H F 1Me-5-Ind G-1,G-2 K-39

H F 2-Nap G-1,G-2 K-40

H F 1Me-5-Ind G-1,G-2

Example L-1 Synthesis of 3-[4-cyclopentyloxy-3-methyl-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. L-1)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 6 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=20:1), Compound A-24 (63 mg), 2-naphthaleneboronic acid (67 mg), 2 M aqueous sodium carbonate (130 μl) and (Ph₃P)₄Pd (18 mg) were reacted and treated. The obtained substance was reacted with 2 N aqueous sodium hydroxide μl) and treated according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. L-1, 25 mg).

Example L-2 Synthesis of methyl 3-[4-cyclopentyloxy-3-methyl-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate (Compound No. L-2)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 12 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Compound No. K-17 (115 mg), methylboronic acid (66 mg, Ald), 2 M aqueous sodium carbonate (0.40 ml) and (Ph₃P)₄Pd (39.4 mg) were reacted and treated to obtain the title compound (Intermediate 52, 84 mg).

Example L-3 Synthesis of 3-[4-cyclopentyloxy-3-methyl-5-(1-methyl-1H-indazol-5-yl)phenyl]propionic acid (Compound No. L-3)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1.5 hours, Compound No. L-2 (82 mg) and 2 N aqueous sodium hydroxide (0.26 ml) were reacted and treated to obtain the title compound (Compound No. L-3, 62 mg).

Examples L-1 to L-95

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-L-1 to Table-L-3.

TABLE L-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass L-1 cPenO H Me 2-Nap L-1 A 5.65 375(M⁺ + 1) L-2 cPenO Me Me 1Me-5-1HIdz L-2 L-3 cPenO H Me 1Me-5-1HIdz L-3 A 4.50 379(M⁺ + 1) L-4 2EtBuO Me Me 2-Nap L-2 L-5 2EtBuO H Me 2-Nap L-3 C 391(M⁺ + 1) L-6 2EtBuO H Me 6-OMe-2-Nap L-2,L-3 L-7 2EtBuO Me Me 5-Ind L-2 L-8 2EtBuO H Me 5-Ind L-3 L-9 2EtBuO Me Me 1Me-5-Ind L-2 L-10 2EtBuO H Me 1Me-5-Ind L-3 L-11 2EtBuO Me Me 5-1HIdz L-2 L-12 2EtBuO H Me 5-1HIdz L-3 L-13 2EtBuO Me Me 1Me-5-1HIdz L-2 L-14 2EtBuO H Me 1Me-5-1HIdz L-3 C 395(M⁺ + 1) L-15 2EtBuO Me Me 5-Bzt L-2 L-16 2EtBuO H Me 5-Bzt L-3 L-17 2EtBuO Me Me 5-2ABzt L-2 L-18 2EtBuO H Me 5-2ABzt L-3 L-19 2EtBuO Me Me 2Me-5-Bzt L-2 L-20 2EtBuO H Me 2Me-5-Bzt L-3 L-21 4Me,cHexO H Me 1Me-5-Ind G-1,G-2 L-22

H Me 2-Nap G-1,G-2 L-23 cHepO H Me 2-Nap G-1,G-2 L-24 cHepO H Me 1Me-5-lnd G-1,G-2 C 406(M⁺ + 1) L-25 3PhPrO H Me 2-Nap G-1,G-2 L-26 4PhBuO H Me 1Me-5-Ind G-1,G-2 L-27

H Me 2-Nap G-1,G-2 L-28 1(4MePh)EtO H Me 1Me-5-Ind G-1,G-2 C 428(M⁺ + 1) L-29 4ClBnO H Me 2-Nap G-1,G-2 L-30 4CF₃BnO H Me 1Me-5-Ind G-1,G-2 L-31 3F,4(OMe)BnO H Me 2-Nap G-1,G-2 L-32

H Me 1Me-5-Ind G-1,G-2 L-33

H Me 2-Nap G-1,G-2 L-34

H Me 2-Nap G-1,G-2 L-35

H Me 1Me-5-Ind G-1,G-2 L-36

H Me 1Me-5-Ind G-1,G-2 L-37

H Me 1Me-5-Ind G-1,G-2 L-38 1-IndanO H Me 2-Nap G-1,G-2 L-39 2-IndanO H Me 2-Nap G-1,G-2 C 423(M⁺ + 1) L-40 2-IndanO H Me 1Me-5-Ind G-1,G-2 L-41 5OMe-2-IndanO H Me 1Me-5-Ind G-1,G-2 L-42 5,6D(OMe)-2-IndanO H Me 2-Nap G-1,G-2 L-43 5F-2-IndaneO H Me 2-Nap G-1,G-2 L-44 5F-2-IndaneO H Me 1Me-5-Ind G-1,G-2 L-45

H Me 1Me-5-Ind G-1,G-2 L-46

H Me 2-Nap G-1,G-2 L-47 2(3MePh)EtO H Me 2-Nap G-1,G-2 L-48 2(3FPh)EtO H Me 1Me-5-Ind G-1,G-2 C 432(M⁺ + 1) L-49 2(2ClPh)EtO H Me 1Me-5-Ind G-1,G-2 L-50 2(4CF₃Ph)EtO H Me 1Me-5-Ind G-1,G-2 L-51 2(2OMePh)EtO H Me 2-Nap G-1,G-2 C 441(M⁺ + 1) L-52 2(4OMePh)EtO H Me 1Me-5-Ind G-1,G-2 L-53 2(2-Nap)EtO H Me 2-Nap G-1,G-2 L-54 2(2-Nap)EtO H Me 1Me-5-Ind G-1,G-2 L-55

H Me 1Me-5-Ind G-1,G-2 L-56

H Me 1Me-5-1HIdz G-1,G-2 C 459(M⁺ + 1) L-57 2(PhS)EtO H Me 2-Nap G-1,G-2 L-58 3PhPrO H Me 1Me-5-Ind G-1,G-2 L-59 2ClBnO H Me 2-Nap G-1,G-2 L-60 2BrBnO H Me 1Me-5-Ind G-1,G-2 L-61 3,5DMeBnO H Me 2-Nap G-1,G-2 L-62 4tBuBnO H Me 2-Nap G-1,G-2 L-63 2CF₃BnO H Me 2-Nap G-1,G-2 L-64 4tBuBnO H Me 1Me-5-Ind G-1,G-2 L-65 4nBuBnO H Me 2-Nap G-1,G-2 C 453(M⁺ + 1) L-66 3,5DClBnO H Me 2-Nap G-1,G-2 L-67 2,3DClBnO H Me 1Me-5-Ind G-1,G-2 L-68 2-NapMeO H Me 1Me-5-Ind G-1,G-2 L-69 1-NapMeO H Me 2-Nap G-1,G-2 L-70 2PhBnO H Me 1Me-5-Ind G-1,G-2 L-71 4PhBnO H Me 2-Nap G-1,G-2 C 476(M⁺ + 1) L-72 5OMe-2-IndanO H Me 1Me-5-Ind G-1,G-2 L-73 5F-2-IndaneO H Me 2-Nap G-1,G-2 L-74

H Me 2-Nap G-1,G-2 C 401 (M⁺ + 1) L-75

H Me 1Me-5-Ind G-1,G-2 L-76

H Me 2-Nap G-1,G-2 L-77

H Me 1Me-5-Ind G-1,G-2 L-78

H Me 2-Nap G-1,G-2 L-79

H Me 1Me-5-Ind G-1,G-2 L-80

H Me 2-Nap G-1,G-2 L-81

H Me 1Me-5-Ind G-1,G-2 L-82

H Me 2-Nap G-1,G-2 C 412(M⁺ + 1) L-83

H Me 1Me-5-Ind G-1,G-2 L-84

H Me 2-Nap G-1,G-2 L-85

H Me 1Me-5-Ind G-1,G-2 L-86

H Me 2-Nap G-1,G-2 L-87

H Me 1Me-5-Ind G-1,G-2 L-88

H Me 2-Nap G-1,G-2 L-89

H Me 1Me-5-Ind G-1,G-2 C 415(M⁺ + 1) L-90

H Me 2-Nap G-1,G-2 L-91

H Me 1Me-5-Ind G-1,G-2 L-92

H Me 2-Nap G-1,G-2 L-93

H Me 1Me-5-Ind G-1,G-2 C 435(M⁺ + 1) L-94

H Me 2-Nap G-1,G-2 L-95

H Me 1Me-5-Ind G-1,G-2

Examples M-1 to M-32

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-M-1 and Table-M-2.

TABLE M-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass M-1

Me Me 2-Nap G-1 C 478(M⁺ + 1) M-2

H Me 2-Nap G-2 C 464(M⁺ + 1) M-3

Me Me 5-Ind G-1 M-4

H Me 5-Ind G-2 M-5

Me Me 1Me-5-Ind G-1 M-6

H Me 1Me-5-Ind G-2 C 467(M⁺ + 1) M-7

Me Me 5-1HIdz G-1 M-8

H Me 5-1HIdz G-2 M-9

Me Me 1Me-5-1HIdz G-1 M-10

H Me 1Me-5-1HIdz G-2 M-11

H Me 2-Nap G-1,G-2 C 463(M⁺ + 1) M-12

H Me 1Me-5-Ind G-1,G-2 M-13

H Me 2-Nap G-1,G-2 M-14

H Me 1Me-5-Ind G-1,G-2 C 465(M⁺ + 1) M-15

H Me 2-Nap G-1,G-2 M-16

H Me 1Me-5-Ind G-1,G-2 M-17

H Me 2-Nap G-1,G-2 C 464(M⁺ + 1) M-18

H Me 1Me-5-Ind G-1,G-2 M-19

H Me 2-Nap G-1,G-2 M-20

H Me 1Me-5-Ind G-1,G-2 M-21

H Me 2-Nap G-1,G-2 M-22

H Me 1Me-5-Ind G-1,G-2 M-23

H Me 2-Nap G-1,G-2 M-24

H Me 1Me-5-Ind G-1,G-2 C 486(M⁺ + 1) M-25

H Me 2-Nap G-1,G-2 M-26

H Me 1Me-5-Ind G-1,G-2 M-27

H Me 2-Nap G-1,G-2 M-28

H Me 1Me-5-Ind G-1,G-2 M-29

H Me 2-Nap G-1,G-2 M-30

H Me 1Me-5-Ind G-1,G-2 C 472(M⁺ + 1) M-31

H Me 2-Nap G-1,G-2 M-32

H Me 1Me-5-Ind G-1,G-2

Example N-1 Synthesis of methyl 3-{4-[2-(N-acetyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. N-1)

A solution of Compound No. G-107 (32 mg) in methylene chloride (1 ml) was added with pyridine (24 μl, TCI) and acetyl chloride (21 μl, TCI), and stirred for 17 hours. The reaction mixture was added with water (3 ml), and extracted with methylene chloride (10 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 2:1) to obtain the title compound (Compound No. N-1, 28.1 mg).

Example N-2 Synthesis of 3-{4-[2-(N-acetyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionic acid (Compound No. N-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. N-1 (28 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. N-2, 22 mg).

Example N-29 Synthesis of methyl 3-{4-[2-(N-methoxycarbonyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. N-29)

According to the procedure described in the synthesis method of Compound No. N-1, Compound No. G-107 (32 mg), pyridine (23 μl) and methyl chloroformate (23 μl, TCI) were reacted and treated to obtain the title compound (Compound No. N-29, 17.3 mg).

Example N-30 Synthesis of 3-{4-[2-(N-methoxycarbonyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionic acid (Compound No. N-30)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. N-29 (17 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. N-30, 10.1 mg).

Example N-48 Synthesis of methyl 3-{4-[2-(N-methylsulfonyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. N-48)

According to the procedure described in the synthesis method of Compound No. N-1, Compound No. G-107 (32 mg), pyridine (24 μl) and methanesulfonyl chloride (23 μl) were reacted and treated to obtain the title compound (Compound No. N-48, 32.3 mg).

Example N-49 Synthesis of 3-{4-[2-(N-methylsulfonyl-N-phenylamino)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionic acid (Compound No. N-49)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. N-48 (32 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. N-49, 17 mg).

Example N-55 Synthesis of methyl 3-{4-[2-(3-ethyl-1-phenylureido)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. N-55)

According to the procedure described in the synthesis method of Compound No. N-1 provided that the reaction was carried out for 41 hours, Compound No. G-107 (32 mg), pyridine (24 μl) and ethyl isocyanate (24 μl, Nakarai Tecs) were reacted and treated to obtain the title compound (Compound No. N-55, 31.2 mg).

Example N-56 Synthesis of 3-{4-[2-(3-ethyl-1-phenylureido)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionic acid (Compound No. N-56)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. N-55 (31 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. N-56, 15 mg).

Example N-64 Synthesis of methyl 3-{4-[2-(3-ethyl-1-phenylthioureido)ethyloxy]-3 (naphthalen-2-yl)phenyl}propionate (Compound No. N-64)

According to the procedure described in the synthesis method of Compound No. N-1 provided that the reaction was carried out for 41 hours, Compound No. G-107 (32 mg), pyridine (24 μl) and ethyl isothiocyanate (21 μl, Nakarai Tecs) were reacted and treated to obtain the title compound (Compound No. N-64, 27.4 mg).

Example N-65 Synthesis of 3-{4-[2-(3-ethyl-1-phenylthioureido)ethyloxy]-3-(naphthalen-2-yl)phenyl}propionic acid (Compound No. N-65)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. N-64 (27 mg) and 2 N aqueous sodium hydroxide (0.25 ml) were reacted and treated to obtain the title compound (Compound No. N-65, 8.9 mg).

Examples N-1 to N-74

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-1 and Table-N-2.

TABLE N-1

LCMS Exp. A⁵Re Y Zx AR Syn method RTime Mass N-1 COMe Me H 2-Nap N-1 N-2 COMe H H 2-Nap N-2 N-3 COMe Me H 5-Ind N-1 N-4 COMe H H 5-Ind N-2 C 457(M⁺ + 1) N-5 COMe Me H 1Me-5-Ind N-1 N-6 COMe H H 1Me-5-Ind N-2 N-7 COMe Me H 5-1HIdz N-1 N-8 COMe H H 5-1HIdz N-2 N-9 COMe Me H 1Me-5-1HIdz N-1 N-10 COMe H H 1Me-5-1HIdz N-2 N-11 COPh H H 2-Nap N-1,N-2 C 516(M⁺ + 1) N-12 COPh H H 1Me-5-Ind N-1,N-2 N-13 COtBu H H 2-Nap N-1,N-2 N-14 COtBu H H 1Me-5-Ind N-1,N-2 N-15 COiPr H H 2-Nap N-1,N-2 C 496(M⁺ + 1) N-16 COiPr H H 1Me-5-Ind N-1,N-2 N-17 COCH(Et)nBu H H 2-Nap N-1,N-2 N-18 COCH(Et)nBu H H 1Me-5-Ind N-1,N-2 N-19 COCH₂OMe H H 2-Nap N-1,N-2 N-20 COCH₂OMe H H 1Me-5-Ind N-1,N-2 N-21 COCH═CHMe H H 2-Nap N-1,N-2 N-22 COCH═CHMe H H 1Me-5-Ind N-1,N-2 C 483(M⁺ + 1) N-23 COiBu H H 2-Nap N-1,N-2 N-24 COiBu H H 1Me-5-Ind N-1,N-2 N-25 COcPr H H 2-Nap N-1,N-2 N-26 COcPr H H 1Me-5-Ind N-1,N-2 C 483(M⁺ + 1) N-27 CO(CH₂)₂cPen H H 2-Nap N-1,N-2 N-28 CO(CH₂)₂cPen H H 1Me-5-Ind N-1,N-2 N-29 COOMe Me H 2-Nap N-29 N-30 COOMe H H 2-Nap N-30 N-31 COOMe H H 1Me-5-Ind N-29,N-30 N-32 COOPh H H 2-Nap N-29,N-30 C 516(M⁺ + 1) N-33 COOPh H H 1Me-5-Ind N-29,N-30 N-34 CONMe₂ H H 2-Nap N-29,N-30 C 483(M⁺ + 1) N-35 CONMe₂ H H 1Me-5-Ind N-29,N-30 N-36 COOiBu H H 2-Nap N-29,N-30 N-37 COOiBu H H 1Me-5-Ind N-29,N-30 N-38 C(O)SMe H H 2-Nap N-29,N-30 N-39 C(O)SMe H H 1Me-5-Ind N-29,N-30 N-40

H H 2-Nap N-29,N-30 N-41

H H 1Me-5-Ind N-29,N-30 C 528(M⁺ + 1) N-42

H H 2-Nap Int53,N-29 N-43

H H 1Me-5-Ind Int53,N-29 N-44 COO(CH₂)₂OMe H H 2-Nap Int53,N-29 N-45 COO(CH₂)₂OMe H H 1Me-5-Ind Int53,N-29 N-46

H H 2-Nap Int53,N-29 N-47

H H 1Me-5-Ind Int53,N-29 N-48 SO₂Me Me H 2-Nap N-48 N-49 SO₂Me H H 2-Nap N-49 N-50 SO₂Me H H 1Me-5-Ind N-48,N-49 C 493(M⁺ + 1) N-51 SO₂Ph H H 2-Nap N-48,N-49 N-52 SO₂Ph H H 1Me-5-Ind N-48,N-49 N-53 SO₂NMe₂ H H 2-Nap N-48,N-49 C 519(M⁺ + 1) N-54 SO₂NMe₂ H H 1Me-5-Ind N-48,N-49 N-55 CONHEt Me H 2-Nap N-55 N-56 CONHEt H H 2-Nap N-56 C 483(M⁺ + 1) N-57 CONHEt H H 1Me-5-Ind N-55,N-56 N-58 CONHPh H H 2-Nap N-55,N-56 N-59 CONHPh H H 1Me-5-Ind N-55,N-56 N-60 CONHcHex H H 2-Nap N-55,N-56 N-61 CONHcHex H H 1Me-5-Ind N-55,N-56 C 540(M⁺ + 1) N-62 CONHBn H H 2-Nap N-55,N-56 N-63 CONHBn H H 1Me-5-Ind N-55,N-56 N-64 CSNHMe Me H 2-Nap N-64 N-65 CSNHMe H H 2-Nap N-65 N-66 CSNHMe H H 1Me-5-Ind N-64,N65 N-67 CSNHPh H H 2-Nap N-64,N-65 N-68 CSNHPh H H 1Me-5-Ind N-64,N-65 N-69 CSNH(3-Py) H H 2-Nap N-64,N-65 C 548(M⁺ + 1) N-70 CSNH(3-Py) H H 1Me-5-Ind N-64,N-65 N-71 CSNHiPr H H 2-Nap N-64,N-65 N-72 CSNHiPr H H 1Me-5-Ind N-64,N-65 C 516(M⁺ + 1) N-73 CSNHBn H H 2-Nap N-64,N-65 N-74 CSNHBn H H 1Me-5-Ind N-64,N-65

Example P-1 Synthesis of ethyl 3-[2-cyclopentylmethyloxy-3-(naphthalen-2-yl)pyridin-5-yl]propionate (Compound No. P-1)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 14 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), 2-naphthaleneboronic acid (119 mg), Compound No. E-1 (83 mg), 2 M aqueous sodium carbonate (0.3 ml) and (Ph₃P)₄Pd (38.1 mg) were reacted and treated to obtain the title compound (Compound No. P-1, 76 mg).

Example P-2 Synthesis of 3-[2-cyclopentylmethyloxy-3-(naphthalen-2-yl)pyridin-5-yl]propionic acid (Compound No. P-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. P-1 (47.8 mg) and 2 N aqueous sodium hydroxide (0.2 ml) were reacted and treated to obtain the title compound (Compound No. P-2, 20 mg).

Example P-36 Synthesis of ethyl 3-{3-(naphthalen-2-yl)-2-[(R)-1-phenylethyloxy]pyridin-5-yl}propionate (Compound No. P-36)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=6:1), 2-naphthaleneboronic acid (44 mg), Compound No. E-7 (73.3 mg), 2 M aqueous sodium carbonate (120 μl) and (Ph₃P)₄Pd (21.3 mg) were reacted and treated to obtain the title compound (Compound No. P-36, 44 mg).

Example P-37 Synthesis of 3-{3-(naphthalen-2-yl)-2-[(R)-1-phenylethyloxy]pyridin-5-yl}propionic acid (Compound No. P-37)

According to the procedure described in the synthesis method of Intermediate 9, Compound No. P-36 (41.2 mg) and 2 N aqueous sodium hydroxide (0.1 ml) were reacted and treated to obtain the title compound (Compound No. P-37, 38 mg).

Example P-42 Synthesis of ethyl 3-{3-(naphthalen-2-yl)-2-[4-(trifluoromethyl)phenylmethyloxy]pyridin-5-yl}propionate (Compound No. P-42)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=6:1), 2-naphthaleneboronic acid (37.4 mg), Compound No. E-13 (42.4 mg), 2 M aqueous sodium carbonate (90 μl) and (Ph₃P)₄Pd (21.4 mg) were reacted and treated to obtain the title compound (Compound No. P-42, 30.4 mg).

Example P-43 Synthesis of 3-{3-(naphthalen-2-yl)-2-[4-(trifluoromethyl)phenylmethyloxy]pyridin-5-yl}propionic acid (Compound No. P-43)

According to the procedure described in the synthesis method of Intermediate 9, Compound No. P-42 (29.5 mg) and 2 N aqueous sodium hydroxide (0.15 ml) were reacted and treated to obtain the title compound (Compound No. P-43, 24.1 mg).

Examples P-1 to P-50

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-P-1 and Table-P-2.

TABLE P-1

LCMS Exp. RxO Y AR Syn method RTime Mass P-1 cPenMeO Et 2-Nap P-1 P-2 cPenMeO H 2-Nap P-2 A 5.60 376(M⁺ + 1) P-3 cPenMeO Et 5-Ind P-1 A 5.37 393(M⁺ + 1) P-4 cPenMeO H 5-Ind P-2 P-5 cPenMeO Et 1Me-5-Ind P-1 P-6 cPenMeO H 1Me-5-Ind P-2 A 4.90 379(M⁺ + 1) P-7 cPenMeO Et 1Me-5-Ind P-1 P-8 cPenMeO H 5-1HIdz P-2 P-9 cPenMeO Et 5-1HIdz P-1 P-10 cPenMeO H 1Me-5-1HIdz P-2 P-11 cPenMeO Et 5-Bzt P-1 P-12 cPenMeO H 5-Bzt P-2 P-13 cPenMeO Et 5-2ABzt P-1 P-14 cPenMeO H 5-2ABzt P-2 P-15 cPenMeO H 6-IQ P-1, P-2 C 377(M⁺ + 1) P-16 cPenO H 2-Nap P-1, P-2 P-17 cPenO H 5-Ind P-1, P-2 C 351(M⁺ + 1) P-18 cPenO H 1Me-5-Ind P-1, P-2 P-19 cPenO H 5-1HIdz P-1, P-2 P-20 cPenO H 1Me-5-1HIdz P-1, P-2 P-21 cPenO H 5-Bzt P-1, P-2 P-22 cPenO H 5-2ABzt P-1, P-2 P-23 cHexO H 2-Nap P-1, P-2 A 5.51 376(M⁺ + 1) P-24 cHexO H 5-Ind P-1, P-2 P-25 cHexO H 1Me-5-Ind P-1, P-2 P-26 cHexO H 1Me-5-1HIdz P-1, P-2 P-27 2EtBuO H 2-Nap P-1, P-2 A 5.68 378(M⁺ + 1) P-28 2EtBuO H 5-Ind P-1, P-2 P-29 2EtBuO H 1Me-5-Ind P-1, P-2 P-30 iBuO H 2-Nap P-1, P-2 A 5.13 350(M⁺ + 1) P-31 iBuO H 5-Ind P-1, P-2 P-32 iBuO H 1Me-5-Ind P-1, P-2 P-33 iBuO H 1Me-5-1HIdz P-1, P-2 P-34 BnO H 2-Nap P-1, P-2 P-35 BnO H 1Me-5-Ind P-1, P-2 P-36 (R)1PhEtO Et 2-Nap P-36 P-37 (R)1PhEtO H 2-Nap P-37 P-38 (S)1PhEtO H 2-Nap P-36, P-37 A 5.31 398(M⁺ + 1) P-39 (S)1PhEtO H 1Me-5-Ind P-36, P-37 A 4.75 401(M⁺ + 1) P-40 2MeBnO H 2-Nap P-1, P-2 P-41 2MeBnO H 1Me-5-Ind P-1, P-2 P-42 4CF3BnO Et 2-Nap P-42 P-43 4CF3BnO H 2-Nap P-43 A 5.52 452(M⁺ + 1) P-44 4CF3BnO H 1Me-5-Ind P-1, P-2 P-45 3PhBuO H 1Me-5-Ind P-1, P-2 P-46 2(2-Nap)EtO H 2-Nap P-1,P-2 P-47 2(2-Nap)EtO H 1Me-5-Ind P-1, P-2 P-48 2(2FPh)EtO H 2-Nap P-1, P-2 P-49 2(2FPh)EtO H 5-Ind P-1, P-2 A 4.18 405(M⁺ + 1) P-50 2(2FPh)EtO H 1Me-5-Ind P-1, P-2

Example Q-1 Synthesis of methyl 3-[4-methoxy-3-(naphthalen-2-yl)-5-nitrophenyl]propionate (Intermediate 49)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 15 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), Intermediate 21 (2.65 g), 2-naphthaleneboronic acid (2.87 g), 2 M aqueous sodium carbonate (7.5 ml) and (Ph₃P)₄Pd (960 mg) were reacted and treated to obtain the title compound (Intermediate 49, 2.47 g).

Synthesis of 3-[4-methoxy-3-(naphthalen-2-yl)-5-nitrophenyl]propionic acid (Intermediate 50)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 40 minutes, Intermediate 49 (2.45 g) and 2 N aqueous sodium hydroxide (6.7 ml) were reacted and treated to obtain the title compound (Intermediate 60, 1.96 g).

Synthesis of methyl 3-[4-hydroxy-3-(naphthalen-2-yl)-5-nitrophenyl]propionate (Intermediate 51)

According to the procedure described in the synthesis method of Intermediate 10 provided that the reaction was carried out for 3 hours, pyridine (10 ml), concentrated hydrochloric acid (10 ml), and Intermediate 50 (1.00 g) were reacted and treated to obtain crude powder substance. This substance was reacted with thionyl chloride (282 μl) in methanol and treated according to the procedure described in the synthesis method of Intermediate 1 to obtain the title compound (Intermediate 51, 306 mg).

Synthesis of methyl 3-[4-cyclopentyloxy-3-(naphthalen-2-yl)-5-nitrophenyl]propionate (Compound No. Q-1)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 15.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=19:1), Intermediate 51 (84 mg), Ph₃P (125 mg), cyclopentanol (50 μl) and 40% DIAD (224 μl) were reacted and treated to obtain the title compound (Compound No. Q-1, 90 mg).

Example Q-2 Synthesis of methyl 3-[3-amino-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. Q-2)

A solution of Compound No. Q-1 (59.1 mg) in methanol (5 ml) was added with platinum oxide (5 mg, Ald), and stirred at room temperature for 30 minutes under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. Q-2, 49 mg).

Example Q-3 Synthesis of 3-[3-amino-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. Q-3)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. Q-2 (40 mg) and 2 N aqueous sodium hydroxide (150 μl) were reacted and treated to obtain the title compound (Compound No. Q-3, 38 mg).

Example Q-4 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)-5-nitrophenyl]propionate (Compound No. Q-4)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Compound No. A-28 (187 mg), 5-indoleboronic acid (143 mg), 2 M aqueous sodium carbonate (400 μl) and (Ph₃P)₄Pd (51 mg) were reacted and treated to obtain the title compound (Compound No. Q-4, 192 mg).

Example Q-5 Synthesis of methyl 3-[3-amino-4-cyclopentyloxy-5-(1H-indol-5-yl)phenyl]propionate (Compound No. Q-5)

According to the procedure described in the synthesis method of Compound No. Q-2 with the modification that the purification was performed by column chromatography (Quad, hexane:ethyl acetate=2:1), Compound No. Q-4 (59.1 mg) and platinum oxide (5 mg) were reacted and treated to obtain the title compound (Compound No. Q-5, 49.3 mg).

Example Q-6 Synthesis of 3-[3-amino-4-cyclopentyloxy-5-(1H-indol-5-yl)phenyl]propionic acid (Compound No. Q-6)

According to the procedure described in the synthesis method of Intermediate 9, Compound No. Q-5 (44 mg) and 2 N aqueous sodium hydroxide (150 μl) were reacted and treated to obtain the title compound (Compound No. Q-6, 41 mg).

Example Q-8 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1-methyl-1H-indazol-5-yl)-5-nitrophenyl]propionate (Compound No. Q-8)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=3:1), Compound No. A-28 (182 mg), 1-methyl-5-indazoleboronic acid (152 mg), 2 M aqueous sodium carbonate (400 μl) and (Ph₃P)₄Pd (58.9 mg) were reacted and treated to obtain the title compound (Compound No. Q-8, 181 mg).

Example Q-9 Synthesis of methyl 3-[3-amino-4-cyclopentyloxy-5-(1-methyl-1H-indazol-5-yl)phenyl]propionic acid (Compound No. Q-9)

A solution of Compound No. Q-8 (578 mg) in a mixture of ethyl acetate (2 ml) and methanol (5 ml) was added with Raney 2800 nickel (230 mg) and stirred at room temperature for 6 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Compound No. Q-9, 484 mg).

Example Q-10 Synthesis of 3-[3-amino-4-cyclopentyloxy-5-(1H-indazol-5-yl)phenyl]propionic acid (Compound No. Q-10)

According to the procedure described in the synthesis method of Intermediate 9, Compound No. Q-9 (56 mg) and 2 N aqueous sodium hydroxide (200 μl) were reacted and treated to obtain the title compound (Compound No. Q-10, 50 mg).

Example Q-47 Synthesis of methyl 3-[4-benzyloxy-3-(naphthalen-2-yl)-5-nitrophenyl]propionate (Compound No. Q-47)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 12 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=8:1), Compound No. B-95 (6.00 g), 2-naphthaleneboronic acid (4.11 g), 2 M aqueous sodium carbonate (13.5 ml) and (Ph₃P)₄Pd (1.36 g) were reacted and treated to obtain the title compound (Compound No. Q-47, 5.81 g).

Example Q-48 Synthesis of methyl 3-[3-amino-4-benzyloxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. Q-48)

According to the procedure described in the synthesis method of Compound No. Q-9 with the modifications that the reaction was carried out for 20 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=2:1), Compound No. Q-47 (5.04 g) and Raney 2800 nickel (2.50 g) were reacted and treated to obtain the title compound (Compound No. Q-48, 4.21 g).

Example Q-1 to Q-52

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-Q-1.

TABLE Q-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass Q-1 cPenO Me NO2 2-Nap Q-1 Q-2 cPenO Me NH2 2-Nap Q-2 Q-3 cPenO H NH2 2Nap Q-3 A 4.78 376(M⁺ + 1) Q-4 cPenO Me NO2 5-Ind Q-4 Q-5 cPenO Me NH2 5-Ind Q-5 Q-6 cPenO H NH2 5-Ind Q-6 A 3.75 365(M⁺ + 1) Q-7 cPenO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 A 4.19 379(M⁺ + 1) Q-8 cPenO Me NO2 1Me-5-1HIdz Q-8 Q-9 cPenO Me NH2 1Me-5-1HIdz Q-9 Q-10 cPenO H NH2 1Me-5-1HIdz Q-10 Q-11 cPenO H NH2 5-1HIdz Q-8,Q-9,Q-10 Q-12 cPenO H NH2 5-Bzt Q-8,Q-9,Q-10 Q-13 cPenO H NH2 5-2ABzt Q-8,Q-9,Q-10 Q-14 cPenO H NH2 2Me-5-Bzt Q-8,Q-9,Q-10 Q-15 cHexO H NH2 2-Nap Q-1,Q-2,Q-3 A 5.66 404(M⁺ + 1) Q-16 cHexO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-17 cHexO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 Q-18 2EtBuO H NH2 2-Nap Q-1,Q-2,Q-3 Q-19 2EtBuO H NH2 5-Ind Q-4,Q-5,Q-6 A 4.26 381(M⁺ + 1) Q-20 2EtBuO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-21 2EtBuO H NH2 5-1HIdz Q-8,Q-9,Q-10 Q-22 2EtBuO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 Q-23 2EtBuO H NH2 5-Bzt Q-8,Q-9,Q-10 Q-24 2EtBuO H NH2 5-2ABzt Q-8,Q-9,Q-10 Q-25 2EtBuO H NH2 2Me-5-Bzt Q-8,Q-9,Q-10 Q-26 iBuO H NH2 2-Nap Q-1,Q-2,Q-3 A 4.82 364(M⁺ + 1) Q-27 iBuO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-28 iBuO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 A 3.66 368(M⁺ + 1) Q-29 (S)1PhEtO H NH2 2-Nap Q-1,Q-2,Q-3 A 4.87 412(M⁺ + 1) Q-30 (S)1PhEtO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 A 4.31 415(M⁺ + 1) Q-31 (S)1PhEtO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 A 3.76 416(M⁺ + 1) Q-32 4CF₃BnO H NH2 2-Nap Q-1,Q-2,Q-3 A 5.26 466(M⁺ + 1) Q-33 4CF₃BnO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 A 4.20 455(M⁺ + 1) Q-34 4CF₃BnO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 Q-35 2-IndanO H NH2 2-Nap Q-1,Q-2,Q-3 A 5.10 424(M⁺ + 1) Q-36 2-IndanO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 A 4.63 427(M⁺ + 1) Q-37 2-IndanO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 A 4.14 428 (M⁺ + 1) Q-38 5OMe-2-IndanO H NH2 2-Nap Q-1,Q-2,Q-3 Q-39 5,6(OMe)-2-IndanO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-40 5F-2-IndanO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 Q-41 2(4FPh)EtO H NH2 2-Nap Q-1,Q-2,Q-3 Q-42 2(4FPh)EtO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-43 2(4FPh)EtO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 A 4.48 448(M⁺ + 1) Q-44 2(4DMAPh)EtO H NH2 2-Nap Q-1,Q-2,Q-3 A 4.28 455(M⁺ + 1) Q-45 2(4DMAPh)EtO H NH2 1Me-5-Ind Q-4,Q-5,Q-6 Q-46 2(4DMAPh)EtO H NH2 1Me-5-1HIdz Q-8,Q-9,Q-10 A 3.12 459(M⁺ + 1) Q-47 BnO Me NO2 2-Nap Q-47 Q-48 BnO Me NH2 2-Nap Q-48 Q-49 BnO H NH2 2-Nap Q-3 Q-50 BnO Me NO2 1Me-5-1HIdz Q-47 Q-51 BnO Me NH2 1Me-5-1HIdz Q-48 Q-52 BnO H NH2 1Me-5-1HIdz Q-10

Example S-1 Synthesis of methyl 3-{4-benzyloxy-3-(naphthalen-2-yl)-5-[N-(2,2,2-trifluoroacetyl)amino]phenyl}propionate (Intermediate 52)

According to the procedure described in the synthesis method of Compound No. B-103 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=4:1), Compound No. Q-48 (4.18 g), triethylamine (4.65 ml) and trifluoroacetic anhydride (7.40 ml) were reacted and treated to obtain the title compound (Intermediate 52, 4.72 g).

Synthesis of methyl 3-{4-hydroxy-3-(naphthalen-2-yl)-5-[N-(2,2,2-trifluoroacetyl)amino]phenyl}propionate (Intermediate 53)

A solution of Intermediate 52 (3.20 g) in a mixture of ethyl acetate (50 ml) and methanol (25 ml) was added with 10% palladium/carbon (98 mg), and stirred at room temperature for 2 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 53, 2.39 g).

Synthesis of methyl 3-{4-cyclopentyloxy-3-(naphthalen-2-yl)-5-[N-(2,2,2-trifluoroacetyl)amino]phenyl}propionate (Intermediate 54)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 15.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=19:1), Intermediate 53 (84 mg), Ph₃P (125 mg), cyclopentanol (50 μl) and 40% DIAD (224 μl) were reacted and treated to obtain the title compound (Intermediate 54, 90 mg).

Synthesis of methyl 3-{4-cyclopentyloxy-3-[N-methyl-N-(2,2,2-trifluoroacetyl)amino]-5-(naphthalen-2-yl)phenyl}propionate (Intermediate 55)

A solution of Intermediate 54 (208 mg) in DMF (5 ml) was added with 60% sodium hydride (21 mg) under ice cooling, and stirred for 20 minutes. This reaction mixture was added dropwise with methyl iodide (150 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was poured into ice water, and ethyl acetate (100 ml) was added for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=5:1) to obtain the title compound (Intermediate 55, 200 mg).

Synthesis of 3-[4-cyclopentyloxy-3-(N-methylamino)-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-1)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 6 hours, Intermediate 55 (198 mg) and 2 N aqueous sodium hydroxide (800 μl) were reacted and treated to obtain the title compound (Compound No. S-1, 38 mg).

Example S-3 Synthesis of methyl 3-[3-acetylamino-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. S-3)

A solution of Compound No. Q-2 (81 mg) in methylene chloride (2 ml) was added with N-methylmorpholine (33 μl, WAKO), and added with acetyl chloride (22 μl) under ice cooling. The reaction mixture was stirred for 10 minutes, then warmed to room temperature, and further stirred for 18 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (100 ml), and added with ethyl acetate (150 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 6:1) to obtain the title compound (Compound No. S-3, 85 mg).

Example S-4 Synthesis of 3-[3-acetylamino-4-cyclopentylmethyloxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-4)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 15 hours, Compound No. S-3 (80 mg) and 2 N aqueous sodium hydroxide (400 μl) were reacted and treated to obtain the title compound (Compound No. S-4, 75 mg).

Example S-5 Synthesis of 3-[4-cyclopentyloxy-3-formylamino-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-5)

A solution of Compound No. Q-2 (90 mg) in DMF (5 ml) was added with a mixture of formic acid (200 μl) and acetic anhydride (100 μl) under ice cooling. The reaction mixture was stirred 10 minutes, then warmed to room temperature, and further stirred for 18 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (100 ml), and added with ethyl acetate (150 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=5:1). The obtained substance was reacted and treated with 2N aqueous sodium hydroxide (400 μl) according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. S-5, 65 mg).

Example S-6 Synthesis of methyl 3-[3-(2-acetoxyacetylamino)-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. S-6)

According to the procedure described in the synthesis method of Intermediate 70, Compound No. Q-2 (88 mg), N-methylmorpholine (36 μl) and acetoxyacetyl chloride (35 μl, Ald) were reacted and treated to obtain the title compound (Compound No. S-6, 75 mg).

Example S-7 Synthesis of 3-[4-cyclopentyloxy-3-(2-hydroxyacetylamino)-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-7)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 15.5 hours, Compound No. S-6 (102 mg) and 2 N aqueous sodium hydroxide (500 μl) were reacted and treated to obtain the title compound (Compound No. S-7, 80 mg).

Example S-8 Synthesis of 3-[3-carbamoylamino-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-8)

A solution of Compound No. Q-2 (100 mg) in a mixture of acetic acid (2 ml) and purified water (0.4 ml) was added with potassium cyanate (45 mg, Wako Pure Chemical Industries), and stirred at room temperature for 1 hour. The reaction mixture was poured into water (50 ml) containing ice, and extracted with isopropyl ether (150 ml×2). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The obtained substance was reacted with 2 N aqueous sodium hydroxide (300 μl) and treated according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. S-8, 70 mg).

Example S-9 Synthesis of methyl 3-[4-cyclopentyloxy-3-methylsulfonylamino-5-(naphthalen-2-yl)phenyl]propionate (Compound No. S-9)

A solution of Compound No. Q-2 (81 mg) in methylene chloride (2 ml) was added with pyridine (300 μl), and then added with methanesulfonyl chloride (40 μl) under ice cooling. The reaction mixture was stirred for 10 minutes, then warmed to room temperature, and further stirred for 2 hours. The reaction mixture was poured into 1 N hydrochloric acid, and added with ethyl acetate (150 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, and saturated brine, and dried, and then the solvent of the organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=13:2) to obtain the title compound (Compound No. S-9, 96 mg).

Synthesis of 3-[4-cyclopentyloxy-3-methylsulfonylamino-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-10)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out at room temperature for 17.5 hours and at 60° C. for 3 hours, Compound No. S-9 (81 mg) and 2 N aqueous sodium hydroxide (400 μl) were reacted and treated to obtain the title compound (Compound No. S-10, 80 mg).

Example S-11 Synthesis of 3-[4-cyclopentyloxy-3-(N,N-dimethylsulfamoylamino)-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-11)

A solution of Compound No. Q-2 (163 mg) in pyridine (5 ml) was successively added with 4-dimethylaminopyridine (104 mg, TCI) and dimethylsulfamoyl chloride (520 μl, TCI), and stirred for 5 days. The reaction mixture was added with water (30 ml) and ethyl acetate (90 ml) for extraction. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1). The obtained substance was reacted with 2 N aqueous sodium hydroxide (300 μl) and treated according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. S-11, 105 mg).

Example S-12 Synthesis of 3-[4-cyclopentyloxy-3-(N,N-dimethylamino)-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. S-12)

A solution of Compound No. Q-2 (60 mg) in DMF (3 ml) was added with 60% sodium hydride (26 mg) under ice cooling, and stirred for 10 minutes. The reaction mixture was added with methyl iodide (100 μl), stirred for 10 minutes, then warmed to 60° C., and further stirred for 2 hours. The reaction mixture was poured into water (20 ml), and ethyl acetate (50 ml) was added for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=8:1). The obtained substance was reacted with 2 N aqueous sodium hydroxide (150 μl) and treated according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. S-12, 46 mg).

Synthesis of methyl 3-{4-benzyloxy-3-(1-methyl-1H-indazol-5-yl)-5-[N-(2,2,2-trifluoroacetyl)amino]phenyl}propionate (Intermediate 56)

According to the procedure described in the synthesis method of Compound No. B-103 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=3:1), Compound No. Q-51 (2.09 g), triethylamine (3.70 ml) and trifluoroacetic anhydride (2.35 ml) were reacted and treated to obtain the title compound (Intermediate 56, 2.36 g).

Synthesis of methyl 3-{4-hydroxy-3-(1-methyl-1H-indazol-5-yl)-5-[N-(2,2,2-trifluoroacetyl)amino]phenyl}propionate (Intermediate 57)

A solution of Intermediate 56 (1.62 g) in a mixture of ethyl acetate (10 ml) and methanol (3 ml) was added with 10% palladium/carbon (29 mg), and stirred at room temperature for 17 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 57, 1.19 g).

Examples S-1 to S-73

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-S-1 and Table-S-2.

TABLE S-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass S-1 cPenO H NHMe 2-Nap S-1 S-2 cPenO H NHEt 2-Nap S-1 S-3 cPenO Me NHAc 2-Nap S-3 S-4 cPenO H NHAc 2-Nap S-4 C 421(M⁺ + 1) S-5 cPenO H NHCHO 2-Nap S-5 C 407(M⁺ + 1) S-6 cPenO H NHCOCH₂OAc 2-Nap S-6 S-7 cPenO H NHCOCH₂OH 2-Nap S-7 C 437(M⁺ + 1) S-8 cPenO H NHCONH₂ 2-Nap S-8 C 422(M⁺ + 1) S-9 cPenO Me NHSO₂Me 2-Nap S-9 S-10 cPenO H NHSO₂Me 2-Nap S-10 C 456(M⁺) S-11 cPenO H NHSO₂NMe₂ 2-Nap S-11 C 483(M⁺ + 1) S-12 cPenO H NMe₂ 2-Nap S-12 S-13 cPenO H NHMe 1Me-5-Ind S-1 S-14 cPenO H NMe₂ 1Me-5-Ind S-12 C 407(M⁺ + 1) S-15 cPenO H NHMe 1Me-5-1HIdz S-1 C 394(M⁺ + 1) S-16 cPenO H NMe₂ 1Me-5-1HIdz S-12 S-17 cPenO H NHMe 5-Bzt S-1 S-18 cPenO H NMe₂ 5-Bzt S-12 S-19 cPenO H NHMe 5-2ABzt S-1 S-20 cPenO H NMe₂ 5-2ABzt S-12 S-21 cPenO H NHMe 2Me-5-Bzt S-1 S-22 cPenO H NMe₂ 2Me-5-Bzt S-12 S-23 cPenMeO H NHMe 1Me-5-Ind S-1 S-24 cPenMeO H NMe₂ 1Me-5-Ind S-12 S-25 cPenMeO H NHMe 1Me-5-1HIdz S-1 S-26 cPenMeO H NMe₂ 1Me-5-1HIdz S-12 S-27 cHexO H NHMe 2-Nap S-1 S-28 cHexO H NMe₂ 2-Nap S-12 S-29 cHexO H NHMe 1Me-5-Ind S-1 C 421(M⁺ + 1) S-30 cHexO H NMe₂ 1Me-5-Ind S-12 S-31 cHexO H NHMe 1Me-5-1HIdz S-1 S-32 cHexO H NMe₂ 1Me-5-1HIdz S-12 S-33 2EtBuO H NHMe 2-Nap S-1 C 406(M⁺ + 1) S-34 2EtBuO H NHMe 6-OMe-2-Nap S-1 S-35 2EtBuO H NHMe 1Me-5-Ind S-1 S-36 2EtBuO H NHMe 5-Bzt S-1 S-37 2EtBuO H NHMe 1Me-5-1HIdz S-1 S-38 iBuO H NHMe 2-Nap S-1 S-39 iBuO H NMe₂ 2-Nap S-12 C 392(M⁺ + 1) S-40 iBuO H NHMe 1Me-5-Ind S-1 C 381(M⁺ + 1) S-41 iBuO H NMe₂ 1Me-5-Ind S-12 S-42 iBuO H NHMe 1Me-5-1HIdz S-1 S-43 iBuO H NMe₂ 1Me-5-1HIdz S-12 S-44 1PhEtO H NHMe 2-Nap S-1 C 426(M⁺ + 1) S-45 1PhEtO H NMe₂ 2-Nap S-12 S-46 1PhEtO H NHMe 1Me-5-Ind S-1 S-47 1PhEtO H NMe₂ 1Me-5-Ind S-12 C 443(M⁺ + 1) S-48 1PhEtO H NHMe 1Me-5-1HIdz S-1 C 429(M⁺ + 1) S-49 1PhEtO H NMe₂ 1Me-5-1HIdz S-12 S-50 4CF₃BnO H NHMe 2-Nap S-1 S-51 4CF₃BnO H NMe₂ 2-Nap S-12 S-52 4CF₃BnO H NHMe 1Me-5-Ind S-1 S-53 4CF₃BnO H NMe₂ 1Me-5-Ind S-12 C 497(M⁺ + 1) S-54 4CF₃BnO H NHMe 1Me-5-1HIdz S-1 S-55 4CF₃BnO H NMe₂ 1Me-5-1HIdz S-12 S-56 2-IndanO H NHMe 2-Nap S-1 S-57 2-IndanO H NMe₂ 2-Nap S-12 S-58 2-IndanO H NHMe 1Me-5-Ind S-1 C 441(M⁺ + 1) S-59 2-IndanO H NMe₂ 1Me-5-Ind S-12 S-60 2-IndanO H NHMe 1Me-5-1HIdz S-1 A 4.16 442(M⁺ + 1) S-61 2-IndanO H NMe₂ 1Me-5-1HIdz S-12 A 4.18 456(M⁺ + 1) S-62 2(4FPh)EtO H NHMe 2-Nap S-1 S-63 2(4FPh)EtO H NMe₂ 2-Nap S-12 C 458(M⁺ + 1) S-64 2(4FPh)EtO H NHMe 1Me-5-Ind S-1 C 447(M⁺ + 1) S-65 2(4FPh)EtO H NMe₂ 1Me-5-Ind S-12 S-66 2(4FPh)EtO H NHMe 1Me-5-1HIdz S-1 S-67 2(4FPh)EtO H NMe₂ 1Me-5-1HIdz S-12 S-68 2(4DMAPh)EtO H NHMe 2-Nap S-1 C 469(M⁺ + 1) S-69 2(4DMAPh)EtO H NMe₂ 2-Nap S-12 S-70 2(4DMAPh)EtO H NHMe 1Me-5-Ind S-1 S-71 2(4DMAPh)EtO H NMe₂ 1Me-5-Ind S-12 C 486(M⁺ + 1) S-72 2(4DMAPh)EtO H NHMe 1Me-5-1HIdz S-1 C 473(M⁺ + 1) S-73 2(4DMAPh)EtO H NMe₂ 1Me-5-1HIdz S-12

Example T-1 Synthesis of 3-[4-cyclopentylmethyloxy-3-hydroxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. T-1)

A solution of Compound No. Q-2 (403 mg) in acetic acid (1.5 ml) was added with 20% sulfuric acid (1.0 ml). This reaction mixture was added dropwise with an aqueous solution (0.5 ml) of sodium nitrite (76 mg) over 10 minutes while keeping the temperature of the reaction mixture below 10° C., and further stirred for 5 minutes. This reaction solution was added to a solution of sodium acetate (328 mg) in acetic acid (3.5 ml) heated and stirred at 100° C. beforehand, and further stirred for 10 minutes with heating. The reaction solution was poured into ice water (50 ml), and extracted with isopropyl ether (100 ml×2). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1). The obtained substance was reacted with 2 N aqueous sodium hydroxide (500 μl) and treated according to the procedure described in the synthesis method of Intermediate 9 to obtain the title compound (Compound No. T-1, 78 mg).

Example T-2 Synthesis of ethyl 3-[3-acetoxy-4-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]propionate (Intermediate 58)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=9:1), Compound No. B-114 (160 mg), 2-naphthaleneboronic acid (382 mg, Ald), 2 M aqueous sodium carbonate (0.7 ml) and (Ph₃P)₄Pd (105 mg) were reacted and treated to obtain the title compound (Intermediate 58, 152 mg).

Synthesis of 3-[4-cyclopentyloxy-3-hydroxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. T-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Intermediate 58 (146 mg) and 2 N aqueous sodium hydroxide (0.35 ml) were reacted and treated to obtain the title compound (Compound No. T-2, 135 mg).

Example T-31 Synthesis of ethyl 3-[4-cyclopentyloxy-3-methoxy-5-(naphthalen-2-yl)phenyl]propionate (Compound No. T-31)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 14 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=9:1), Compound No. A-25 (210 mg), 2-naphthaleneboronic acid (184 mg), 2 M aqueous sodium carbonate (0.5 ml) and (Ph₃P)₄Pd (65.3 mg) were reacted and treated to obtain the title compound (Compound No. T-31, 181 mg).

Example T-32 Synthesis of 3-[4-cyclopentyloxy-3-methoxy-5-(naphthalen-2-yl)phenyl]propionic acid (Compound No. T-32)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. T-31 (166 mg) and 2 N aqueous sodium hydroxide (0.45 ml) were reacted and treated to obtain the title compound (Compound No. T-32, 135 mg).

Example T-33 Synthesis of 4-(t-butyldimethylsilyloxy)-3-(1H-indol-5-yl)-5-methoxybenzaldehyde (Intermediate 59)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 12.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=7:1), 5-indoleboronic acid (1.29 g), Intermediate 16 (1.75 g), 2 M aqueous sodium carbonate (4.8 ml) and (Ph₃P)₄Pd (400 mg) were reacted and treated to obtain the title compound (Intermediate 59, 910 mg).

Synthesis of ethyl 3-[4-(t-butyldimethylsilyloxy)-3-(1H-indol-5-yl)-5-methoxyphenyl]acrylate (Intermediate 60)

According to the procedure described in the synthesis method of Intermediate 7 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=3:1), Intermediate 59 (910 mg), ethyl diethylphosphonoacetate (500 μl) and 60% sodium hydride (100 mg) were reacted and treated to obtain the title compound (Intermediate 60, 945 mg).

Synthesis of ethyl 3-[4-(t-butyldimethylsilyloxy)-3-(1H-indol-5-yl)-5-methoxyphenyl]propionate (Intermediate 61)

According to the procedure described in the synthesis method of Intermediate 8, Intermediate 60 (945 mg) and 10% palladium/carbon (95 mg) were reacted and treated under hydrogen gas atmosphere to obtain the title compound (Intermediate 61, 940 mg).

Synthesis of ethyl 3-[4-hydroxy-3-(1H-indol-5-yl)-5-methoxyphenyl]propionate (Intermediate 62)

According to the procedure described in the synthesis method of Intermediate 19 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1), Intermediate 61 (750 mg) and a 1 M solution of tetrabutylammonium fluoride in THF (5.0 ml) were reacted and treated to obtain the title compound (Intermediate 62, 555 mg).

Synthesis of ethyl 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)-5-methoxyphenyl]propionate (Compound No. T-33)

According to the procedure described in the synthesis method of Compound No. A-6 with the modifications that the reaction was carried out for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=7:1), Intermediate 62 (340 mg), Ph₃P (1.31 g), cyclopentanol (450 μl) and TMAD (860 mg) were reacted and treated to obtain the title compound (Compound No. T-33, 376 mg).

Example T-34 Synthesis of 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)-5-methoxyphenyl]propionic acid (Compound No. T-34)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. T-33 (99 mg) and 2 N aqueous sodium hydroxide (500 μl) were reacted and treated to obtain the title compound (Compound No. T-34, 76 mg).

Examples T-1 to T-61

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-T-1 and Table T-2.

TABLE T-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass T-1 cPenMeO H OH 2-Nap T-1 A 5.03 382(M⁺ + 1) T-2 cPenO H OH 2-Nap T-2 T-3 cPenO H OH 5-Ind Int73, T-2 C 366(M⁺ + 1) T-4 cPenO H OH 1Me-5-Ind Int73, T-2 T-5 cPenO H OH 5-1HIdz Int73, T-2 T-6 cPenO H OH 1Me-5-Idz Int73, T-2 C 381(M⁺ + 1) T-7 cHexO H OH 2-Nap T-1 T-8 cHexO H OH 1Me-5-Ind T-1 T-9 cHexO H OH 1Me-5-Idz T-1 T-10 2EtBuO H OH 2-Nap T-1 C 393(M⁺ + 1) T-11 2EtBuO H OH 1Me-5-Ind T-1 T-12 2EtBuO H OH 1Me-5-Idz T-1 T-13 iBuO H OH 2-Nap T-1 T-14 iBuO H OH 1Me-5-Ind T-1 T-15 iBuO H OH 1Me-5-Idz T-1 T-16 iPhEtO H OH 2-Nap T-1 T-17 iPhEtO H OH 1Me-5-Ind T-1 C 416(M⁺ + 1) T-18 iPhEtO H OH 1Me-5-Idz T-1 T-19 4CF₃BnO H OH 2-Nap T-1 T-20 4CF₃BnO H OH 1Me-5-Ind T-1 T-21 4CF₃BnO H OH 1Me-5-Idz T-1 T-22 2-IndanO H OH 2-Nap T-1 T-23 2-IndanO H OH 1Me-5-Ind T-1 T-24 2-IndanO H OH 1Me-5-Idz T-1 A 3.91 429(M⁺ + 1) T-25 2(4FPh)EtO H OH 2-Nap T-1 T-26 2(4FPh)EtO H OH 1Me-5-Ind T-1 T-27 2(4FPh)EtO H OH 1Me-5-Idz T-1 T-28 2(4DMAPh)EtO H OH 2-Nap T-1 T-29 2(4DMAPh)EtO H OH 1Me-5-Ind T-1 C 459(M⁺ + 1) T-30 2(4DMAPh)EtO H OH 1Me-5-Idz T-1 T-31 cPenO Et OMe 2-Nap T-31 T-32 cPenO H OMe 2-Nap T-32 T-33 cPenO Et OMe 5-Ind T-33 T-34 cPenO H OMe 5-Ind T-34 T-35 cPenO H OMe 1Me-5-Ind T-33, T-34 A 4.72 394(M⁺ + 1) T-36 cPenO H OMe 5-1HIdz T-31, T-32 T-37 cPenO H OMe 1Me-5-Idz T-31, T-32 T-38 cHexO H OMe 2-Nap T-31, T-32 C 405(M⁺ + 1) T-39 cHexO H OMe 1Me-5-Ind T-33, T-34 T-40 cHexO H OMe 1Me-5-Idz T-31, T-32 T-41 2EtBuO H OMe 2-Nap T-31, T-32 T-42 2EtBuO H OMe 1Me-5-Ind T-33, T-34 T-43 2EtBuO H OMe 1Me-5-Idz T-31, T-32 T-44 iBuO H OMe 2-Nap T-31, T-32 T-45 iBuO H OMe 1Me-5-Ind T-33, T-34 C 382(M⁺ + 1) T-46 iBuO H OMe 1Me-5-1HIdz T-31, T-32 T-47 1PhEtO H OMe 2-Nap T-31, T-32 T-48 1PhEtO H OMe 1Me-5-Ind T-33, T-34 T-49 1PhEtO H OMe 1Me-5-1HIdz T-31, T-32 C 431(M⁺ + 1) T-50 4CF₃BnO H OMe 2-Nap T-31, T-32 T-51 4CF₃BnO H OMe 1Me-5-Ind T-33, T-34 T-52 4CF₃BnO H OMe 1Me-5-1HIdz T-31, T-32 T-53 2-IndanO H OMe 2-Nap T-31, T-32 T-54 2-IndanO H OMe 1Me-5-Ind T-33, T-34 T-55 2-IndanO H OMe 1Me-5-1HIdz T-31, T-32 C 443(M⁺ + 1) T-56 2(4FPh)EtO H OMe 2-Nap T-31, T-32 T-57 2(4FPh)EtO H OMe 1Me-5-Ind T-33, T-34 C 448(M⁺ + 1) T-58 2(4FPh)EtO H OMe 1Me-5-1HIdz T-31, T-32 T-59 2(4DMAPh)EtO H OMe 2-Nap T-31, T-32 C 470(M⁺ + 1) T-60 2(4DMAPh)EtO H OMe 1Me-5-Ind T-33, T-34 T-61 2(4DMAPh)EtO H OMe 1Me-5-1HIdz T-31, T-32

Example U-1 Synthesis of 4-cyclohexylmethyloxy-3-(naphthalen-2-yl)phenylacetonitrile (Intermediate 63)

A solution of Compound No. C-1 (172 mg) in dehydrated THF (5 ml) was added successively with trimethylsilylnitrile (133 μl, TCI) under ice cooling and zinc iodide (16 mg, WAKO) under argon gas atmosphere, stirred for 15 minutes, then warmed to room temperature, and further stirred for 27 hours. The reaction mixture was added with ethyl acetate (90 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. A solution of the residue in anhydrous methylene chloride (5 ml) was added with triethylsilane (240 μl, TCI) under ice cooling and boron trifluoride diethyl ether complex (366 μl, TCI) under argon gas atmosphere, warmed to room temperature, and stirred for 3.5 hours. The reaction mixture was poured into ice water (50 ml), and extracted with ethyl acetate (90 ml). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 63, 116 mg).

Synthesis of 4-cyclohexylmethyloxy-3-(naphthalen-2-yl)phenylacetic acid (Compound No. U-1)

According to the procedure described in the synthesis method of Intermediate 9 with the modifications that the reaction was carried out for 24 hours under reflux by heating, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=2:1), Intermediate 63 (110 mg) and 5 N aqueous sodium hydroxide (900 μl) were reacted and treated to obtain the title compound (Compound No. U-1, 62 mg).

Example U-10 Synthesis of methyl 4-[4-cyclopentylmethyloxy-3-(naphthalen-2-yl)phenyl]butyrate (Compound No. U-10)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 18 hours, and the purification was performed by column chromatography (Quad, hexane:isopropyl ether=8:1), Compound No. F-1 (355 mg), 2-naphthaleneboronic acid (344 mg), 2 M aqueous sodium carbonate (2.1 ml) and (Ph₃P)₄Pd (115 mg) were reacted and treated to obtain the title compound (Compound No. U-10, 392 mg).

Example U-11 Synthesis of 4-[4-cyclopentylmethyloxy-3-(naphthalen-2-yl)phenyl]butyric acid (Compound No. U-11)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3.5 hours, Compound No. U-10 (380 mg) and 2 N aqueous sodium hydroxide (1.0 ml) were reacted and treated to obtain the title compound (Compound No. U-11, 342 mg).

Examples U-1 to U-18

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-U-1.

TABLE U-1

LCMS Exp. RxO Y Zx n AR Syn method RTime Mass U-1 cHexMeO H H 1 2-Nap U-1 C 374(M⁺) U-2 cHexMeO H H 1 1Me-5-Ind Int63,U-1 U-3 cHexMeO H H 1 1Me-5-Idz Int63,U-1 U-4 cPenMeO H H 1 2-Nap Int63,U-1 C 360(M⁺) U-5 cPenMeO H H 1 1Me-5-Ind Int63,U-1 U-6 cPenO H H 1 2-Nap Int63,U-1 U-7 cPenO H H 1 1Me-5-Ind Int63,U-1 C 349(M⁺) U-8 2(4FPh)EtO H H 1 2-Nap Int63,U-1 U-9 2(4FPh)EtO H H 1 1Me-5-Ind Int63,U-1 U-10 cPenMeO Me H 3 2-Nap U-10 C 374(M⁺) U-11 cPenMeO H H 3 2-Nap U-11 C 374(M⁺) U-12 cPenMeO H H 3 1Me-5-Ind U-10,U-11 U-13 cPenO H H 3 2-Nap U-10,U-11 U-14 cPenO H H 3 1Me-5-Ind U-10,U-11 C 377(M⁺) U-15 cHexO H H 3 2-Nap U-10,U-11 U-16 cHexO H H 3 1Me-5-Ind U-10,U-11 U-17 2(4FPh)EtO H H 3 2-Nap U-10,U-11 U-18 2(4FPh)EtO H H 3 1Me-5-Ind U-10,U-11

Example V-1 Synthesis of ethyl 3-[4-cyclohexylmethyloxy-3-(naphthalen-1-yl)phenyl]acrylate (Intermediate 64)

According to the procedure described in the synthesis method of Intermediate 7 provided that the reaction was carried out for 1 hour, Compound No. C-2 (361 mg), ethyl diethylphosphonoacetate (240 μl), 60% sodium hydride (69 mg) were reacted and treated to obtain the title compound (Intermediate 64, 377 mg).

Synthesis of ethyl 3-[4-cyclohexylmethyloxy-3-(naphthalen-1-yl)phenyl]propionate (Compound No. V-1)

According to the procedure described in the synthesis method of Intermediate 8 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=10:1), Intermediate 64 (361 mg) and 10% palladium/carbon (49 mg) were reacted under hydrogen atmosphere and treated to obtain the title compound (Compound No. V-1, 344 mg).

Example V-2 Synthesis of 3-[4-cyclohexylmethyloxy-3-(naphthalen-1-yl)phenyl]propionic acid (Compound No. V-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1.5 hours, Compound No. V-1 (332 mg) and 2 N aqueous sodium hydroxide (900 μl) were reacted and treated to obtain the title compound (Compound No. V-2, 295 mg).

Example V-3 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(6-hydroxynaphthalen-2-yl)phenyl]propionate (Compound No. V-3)

A solution of 2-bromo-6-hydroxynaphthalene (243 mg, TCI) in anhydrous THF (10 ml) was cooled to −78° C., added dropwise with a 1.6 M solution of n-butyllithium in hexane (1.18 ml) over 20 minutes under argon gas atmosphere, and stirred for 30 minutes. The reaction mixture was added dropwise with (^(i)PrO)₃B (1.73 ml) over 10 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 2 hours. The reaction mixture was added with 0.5 M aqueous sulfuric acid (2 ml), and extracted with diethyl ether (40 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 6-hydroxy-2-naphthaleneboronic acid (378 mg). A solution of this substance in ethanol (1 ml), Compound No. A-1 (230 mg), and 2 M aqueous sodium carbonate (2.4 ml) were added with toluene (3 ml) and (Ph₃P)₄Pd (115 mg) and stirred at 100° C. for 13 hours. The reaction mixture was added with ethyl acetate (100 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. V-3, 270 mg).

Example V-4 Synthesis of 3-[4-cyclopentylmethyloxy-3-(6-hydroxynaphthalen-2-yl)phenyl]propionic acid (Compound No. V-4)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 14 hours, Compound No. V-3 (149 mg) and 2 N aqueous sodium hydroxide (370 μl) were reacted and treated to obtain the title compound (Compound No. V-4, 117 mg).

Example V-5 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(5-hydroxynaphthalen-2-yl)phenyl]propionate (Compound No. V-5)

2-Amino-5-hydroxynaphthalene (4.80 g, TCI) was dissolved in 6 N hydrochloric acid (300 ml), added dropwise with an aqueous solution (22.5 ml) of sodium nitrite (2.25 g) over 30 minutes under ice cooling, and stirred for 30 minutes. The reaction mixture was added dropwise with an aqueous solution (75 ml) of potassium iodide (9.90 g, WAKO), stirred for 30 minutes, then warmed to room temperature, and further stirred for 3.5 hours. The reaction mixture was neutralized with aqueous ammonia, and then filtered through a Celite layer. The filtrate was added with ethyl acetate (90 ml×2) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain 1-hydroxy-6-iodonaphthalene (1.48 g). A solution of this substance (539 mg) in anhydrous THF (10 ml) was added with 60% sodium hydride (171 mg) under ice cooling, and stirred for 1 hour. The reaction mixture was cooled to −78° C. under argon gas atmosphere, added dropwise with a 1.6 M solution of n-butyllithium in hexane (3.75 ml) over 10 minutes, and stirred for 30 minutes. The reaction mixture was added dropwise with (^(i)PrO)₃B (1.16 ml) over 10 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 3 hours. The reaction mixture was added with water (3 ml) and 0.5 M aqueous sulfuric acid (7 ml), and extracted with diethyl ether (100 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 7-hydroxy-2-naphthaleneboronic acid. A solution of this substance in ethanol (1 ml), Compound No. A-1 (350 mg), 2 M aqueous sodium carbonate (2.4 ml) and (Ph₃P)₄Pd (116 mg) were reacted and treated according to the procedure described in the synthesis method of Compound No. V-3 with the modifications that the reaction was carried out for 14 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. V-5, 388 mg).

Example V-6 Synthesis of 3-[4-cyclopentylmethyloxy-3-(5-hydroxynaphthalen-2-yl)phenyl]propionic acid (Compound No. V-6)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 12 hours, Compound No. V-5 (355 mg) and 2 N aqueous sodium hydroxide (1.75 ml) were reacted and treated to obtain the title compound (Compound No. V-6, 158 mg).

Example V-7 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(7-hydroxynaphthalen-2-yl)phenyl]propionate (Compound No. V-7)

According to the procedure described in the synthesis method of Compound No. V-5 with the modifications that the reaction was carried out for 4 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=6:1), crude 7-hydroxy-2-naphthaleneboronic acid prepared from 2-bromo-7-hydroxynaphthalene (559 mg, MAYB), a 1.6M solution of n-butyllithium in hexane (3.91 ml) and (^(i)PrO)₃B (1.16 ml), Compound No. A-1 (386 mg), 2 M aqueous sodium carbonate (4.0 ml) and (Ph₃P)₄Pd (195 mg) were reacted and treated to obtain the title compound (Compound No. V-7, 460 mg).

Example V-8 Synthesis of 3-[4-cyclopentylmethyloxy-3-(7-hydroxynaphthalen-2-yl)phenyl]propionic acid (Compound No. V-8)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 27 hours, Compound No. V-7 (176 mg) and 2 N aqueous sodium hydroxide (436 μl) were reacted and treated to obtain the title compound (Compound No. V-8, 109 mg).

Example V-11 Synthesis of methyl 3-{4-cyclohexylmethyloxy-3-[6-(N,N-dimethylcarbamoylmethyloxy)naphthalen-2-yl]phenyl}propionate (Compound No. V-11)

A solution of Compound No. V-3 (185 mg) in DMF (5 ml) was added with potassium carbonate (274 mg), and 2-chloro-N,N-dimethylacetamide (411 μl, KANTO), and stirred at 50° C. for 18 hours. The reaction mixture was added with ethyl acetate (90 ml), and washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by PTLC (chloroform:methanol=10:1) to obtain the title compound (Compound No. V-11, 213 mg).

Example V-12 Synthesis of 3-{4-cyclohexylmethyloxy-3-[6-(N,N-dimethylcarbamoylmethyloxy)naphthalen-2-yl]phenyl}propionic acid (Compound No. V-10)

According to the procedure described in the synthesis method of Intermediate 9 with the modifications that the reaction was carried out at room temperature for 18 hours and at 60° C. for 8 hours, and the purification was performed by PTLC (chloroform:methanol=10:1), Compound No. V-11 (213 mg) and 2 N aqueous sodium hydroxide (420 μl) were reacted and treated to obtain the title compound (Compound No. V-12, 115 mg).

Example V-13 Synthesis of methyl 3-[3-(6-aminonaphthalen-2-yl)-4-cyclopentylmethyloxyphenyl]propionate (Compound No. V-13)

According to a known method described in a publication (Anderson, L. C. et al., J. Am. Chem. Soc, 1943, vol. 65, p. 241), a solution of 2-amino-6-bromonaphthalene (223 mg) obtainable from commercially available 2-bromo-6-hydroxynaphthalene (TCI) in anhydrous THF (10 ml) was added with 30% potassium hydride (191 mg, Ald) under ice cooling, and stirred for 1 hour. The reaction mixture was cooled to −78° C. under argon gas atmosphere, added dropwise with a 1.7 M solution of t-butyllithium in pentane (1.88 ml) over 10 minutes, and stirred for 30 minutes. This reaction mixture was added dropwise with (^(i)PrO)₃B (0.92 ml) over 10 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 3 hours. The reaction mixture was added with water (3 ml) and 0.5 M aqueous sulfuric acid (4 ml), and extracted with diethyl ether (100 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 6-amino-2-naphthaleneboronic acid (402 mg). A solution of this substance in ethanol (0.5 ml), Compound No. A-1 (119 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph₃P)₄Pd (61 mg) were reacted and treated according to the procedure described in the synthesis method of Compound No. V-3 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. V-13, 129 mg).

Example V-14 Synthesis of 3-[3-(6-aminonaphthalen-2-yl)-4-cyclopentylmethyloxyphenyl]propionic acid (Compound No. V-14)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 14 hours, Compound No. V-13 (120 mg) and 2 N aqueous sodium hydroxide (1.75 ml) were reacted and treated to obtain the title compound (Compound No. V-14, 89 mg).

Example V-16 Synthesis of methyl 3-[3-({6-[2-(acetyloxy)acetylamino)naphthalen-2-yl}-4-cyclopentylmethyloxyphenyl)propionate (Intermediate 65)

A solution of Compound No. V-13 (151 mg) in dichloromethane (4 ml) was added with N-methylmorpholine (50 μl), and then added with acetyloxyacetyl chloride (48.3 μl) under ice cooling. The reaction mixture was stirred for 10 minutes, then warmed to room temperature, and further stirred for 4 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (100 ml), and ethyl acetate (150 ml) was added for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by PTLC (hexane:ethyl acetate=1:1) to obtain the title compound (Intermediate 88, 136 mg).

Synthesis of 3-(4-cyclopentylmethyloxy-3-{6-[2-(hydroxyacetyl)amino]naphthalen-2-yl}phenyl)propionic acid (Compound No. V-16)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out at room temperature for 5 hours and at 60° C. for 1 hour, Intermediate 65 (135 mg) and 2 N aqueous sodium hydroxide (1.12 ml) were reacted and treated to obtain the title compound (Compound No. V-16, 102 mg).

Example V-18 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(6-methylsulfonylaminonaphthalen-2-yl)phenyl]propionate (Compound No. V-18)

A solution of Compound No. V-13 (149.1 mg) in 1,2-dichloroethane (5 ml) was added successively with pyridine (500 μl) and methanesulfonyl chloride (62 μl) under ice cooling, stirred for 1.5 hours, then warmed to room temperature, and stirred for 12 hours. The reaction mixture was added with water (30 ml) and ethyl acetate (90 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by PTLC (hexane:ethyl acetate=2:1) to obtain the title compound (Compound No. V-18, 126 mg).

Example V-19 Synthesis of 3-[4-cyclopentylmethyloxy-3-(6-methylsulfonylaminonaphthalen-2-yl)phenyl]propionic acid (Compound No. V-19)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out at room temperature for 3 hours and at 60° C. for 1 hour, Compound No. V-18 (129 mg) and 2 N aqueous sodium hydroxide (535 μl) were reacted and treated to obtain the title compound (Compound No. V-19, 98 mg).

Example V-20 Synthesis of methyl 3-{4-cyclopentylmethyloxy-3-[6-(N,N-dimethylsulfamoylamino)naphthalen-2-yl]phenyl}propionate (Compound No. V-20)

A solution of Compound No. V-13 (165 mg) in pyridine (5 ml) was added successively with 4-dimethylaminopyridine (104 mg, TCI) and dimethylsulfamoyl chloride (520 μl, TCI), stirred for 5 days, and then further stirred at 50° C. for 4 hours. The reaction mixture was added with water (30 ml) and ethyl acetate (90 ml)) for extraction. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 6:1) to obtain the title compound (Compound No. V-20, 125 mg).

Example V-21 Synthesis of 3-{4-cyclopentylmethyloxy-3-[6-(N,N-dimethylsulfamoylamino)naphthalen-2-yl]phenyl}propionic acid (Compound No. V-21)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1.5 hours, Compound No. V-20 (118 mg) and 2 N aqueous sodium hydroxide (460 μl) were reacted and treated to obtain the title compound (Compound No. V-21, 87 mg).

Example V-22 Synthesis of 2-bromo-6-sulfamoylaminonaphthalene (Intermediate 66)

A solution of chlorosulfonyl isocyanate (870 μl, WAKO) in benzene (10 ml) was added dropwise with formic acid (377 μl, WAKO) under ice cooling, warmed to room temperature, stirred and for 19.5 hours, then warmed to 40° C., and further stirred for 4 hours. The reaction mixture was added dropwise with a solution of 2-amino-6-bromonaphthalene (443 mg) in benzene (5 ml) under ice cooling, warmed to room temperature, and stirred 21.5 hours. The reaction mixture was filtered to obtain solid, and the solid was added with ethyl acetate, mixed and filtered again. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 66, 158 mg).

Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(6-sulfamoylaminonaphthalen-2-yl)phenyl]propionate (Compound No. V-22)

According to a procedure described in literature (Miyaura, N. et al., Tetrahedron. Lett., 1997, p. 3447), Compound No. A-1 (209 mg), bis(pinacolate)diboron (177 mg, Ald), [1,1′-bis(diphenylphosphono)ferrocene]palladium(II) dichloride (hereinafter abbreviated as “PdCl₂(dppf)”, 28 mg, TCI) and potassium acetate (182.3 mg, Ald) were added to DMF (6 ml), and heated to 80° C. with stirring under argon gas atmosphere for 5 hours. The reaction mixture was cooled to room temperature, then added with Intermediate 91 (130 mg), PdCl₂(dppf) (30 mg) and 2 M aqueous sodium carbonate (0.9 ml), and heated to 80° C. for 21 hours with stirring under argon gas atmosphere. The reaction mixture was added with ethyl acetate (100 ml), washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=3:1) to obtain the title compound (Compound No. V-22, 46 mg).

Example V-23 Synthesis of 3-[4-cyclopentylmethyloxy-3-(6-sulfamoylaminonaphthalen-2-yl)phenyl]propionic acid (Compound No. V-23)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 24 hours, Compound No. V-22 (41 mg) and 2 N aqueous sodium hydroxide (340 μl) were reacted and treated to obtain the title compound (Compound No. V-23, 22 mg).

Example V-27 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)phenyl]propionate (Compound No. V-27)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out at 80° C. for 5 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=5:1), Compound No. A-5 (367 mg), 5-indoleboronic acid (310 mg, Frontier), 2 M aqueous sodium carbonate (0.9 ml) and (Ph₃P)₄Pd (132 mg) were reacted and treated to obtain the title compound (Compound No. V-27, 340 mg).

Example V-28 Synthesis of 3-[4-cyclopentyloxy-3-(1H-indol-5-yl)phenyl]propionic acid (Compound No. V-28)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. V-27 (330 mg) and 2 N aqueous sodium hydroxide (1.40 ml) were reacted and treated to obtain the title compound (Compound No. V-28, 310 mg).

Example V-29 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1-methyl-1H-indol-5-yl)phenyl]propionate (Compound No. V-29)

A solution of Compound No. V-27 (123 mg) in DMF (5 ml) was added with 60% sodium hydride (19 mg) under ice cooling, and stirred for 10 minutes. The reaction mixture was added dropwise with methyl iodide (100 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was poured into ice water, and ethyl acetate (100 ml) was added for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (Compound No. V-29, 126 mg).

Example V-30 Synthesis of 3-[4-cyclopentyloxy-3-(1-methyl-1H-indol-5-yl)phenyl]propionic acid (Compound No. V-30)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1 hour, Compound No. V-29 (123 mg) and 2 N aqueous sodium hydroxide (330 μl) were reacted and treated to obtain the title compound (Compound No. V-30, 110 mg).

Example V-31 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(1H-indol-4-yl)phenyl]propionate (Compound No. V-31)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 21 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=6:1), Compound No. A-1 (200 mg), 4-indoleboronic acid (170 mg) obtainable from 4-bromoindole (TCI) according to a known method described in a publication (Doll, M. et al., J. Org. Chem., 1999, vol. 64, p. 1372), 2 M aqueous sodium carbonate (550 μl) and (Ph₃P)₄Pd (60 mg) were reacted and treated to obtain the title compound (Compound No. V-31, 214 mg).

Example V-32 Synthesis of 3-[4-cyclopentylmethyloxy-3-(1H-indol-4-yl)phenyl]propionic acid (Compound No. V-32)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1 hour, Compound No. V-31 (210 mg) and 2 N aqueous sodium hydroxide (0.60 ml) were reacted and treated to obtain the title compound (Compound No. V-32, 173 mg).

Example V-33 Synthesis of 4-bromo-1-methyl-1H-indole (Intermediate 67)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 30 minutes, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), 4-bromoindole (5 g), 60% sodium hydride (1.14 g) and methyl iodide (3.18 ml, TCI) were reacted and treated to obtain the title compound (Intermediate 67, 4.95 g).

Synthesis of 1-methyl-1H-indole-4-boronic acid (Intermediate 68)

A solution of Intermediate 67 (4.90 g) in anhydrous THF (30 ml) was cooled to −78° C. under argon gas atmosphere, then added dropwise with a 1.62 M solution of t-butyllithium in pentane (28.8 ml) over 30 minutes, and stirred for 30 minutes. This reaction mixture was added dropwise with (^(i)PrO)₃B (10.77 ml) over 10 minutes, stirred for 1 hour, then warmed to room temperature, and further stirred for 2.5 hours. The reaction mixture was poured into 1.2 N aqueous phosphoric acid (250 ml) containing ice, and extracted with diethyl ether (200 ml×3). The organic layer was extracted with 0.4 N aqueous sodium hydroxide (150 ml×3), and the aqueous layer was made acidic with 5 N hydrochloric acid under ice cooling, and extracted with diethyl ether (200 ml×3) again. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was washed with hexane to obtain the title compound (Intermediate 68, 3.17 g).

Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(1-methyl-1H-indol-4-yl)phenyl]propionate (Compound No. V-33)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 18 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=9:1), Compound No. A-1 (200 mg), Intermediate 68 (185 mg), 2 M aqueous sodium carbonate (550 μl) and (Ph₃P)₄Pd (60 mg) were reacted and treated to obtain the title compound (Compound No. V-33, 208 mg).

Example V-34 Synthesis of 3-[4-cyclopentylmethyloxy-3-(1-methyl-1H-indol-4-yl)phenyl]propionic acid (Compound No. V-34)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. V-33 (200 mg) and 2 N aqueous sodium hydroxide (0.60 ml) were reacted and treated to obtain the title compound (Compound No. V-34, 182 mg).

Example V-43 Synthesis of 3-{4-cyclopentylmethyloxy-3-[1-(2-hydroxyethyl)-1H-indol-5-yl]phenyl}propionic acid (Compound No. V-43)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 1.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=8:1), Compound No. V-27 (144 mg), 60% sodium hydride (38 mg) and ethyl bromoacetate (160 μl, TCI) were reacted and treated to obtain an oily substance. This substance was reacted with 2 N aqueous sodium hydroxide (300 μl) and treated according to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 1 hour to obtain the title compound (Compound No. V-43, 36 mg).

Example V-44 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(3-formyl-1H-indol-5-yl)phenyl]propionate (Compound No. V-44)

A solution of Compound No. V-27 (75 mg) in DMF (6 ml) was added dropwise with phosphoryl chloride (30 μl, TCI) under ice cooling, stirring for 1 hour, then warmed to 35° C., and further stirred for 1 hour. The reaction mixture was added with 1 N aqueous sodium hydroxide (3 ml) containing ice, and extracted with ethyl acetate (90 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (Compound No. V-44, 86 mg).

Example V-45 Synthesis of 3-[4-cyclopentylmethyloxy-3-(3-formyl-1H-indol-5-yl)phenyl]propionic acid (Compound No. V-45)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. V-44 (86 mg) and 2 N aqueous sodium hydroxide (110 μl) were reacted and treated to obtain the title compound (Compound No. V-45, 60 mg).

Example V-47 Synthesis of methyl 3-[3-(3-acetyl-1H-indol-5-yl)-4-cyclopentylmethyloxyphenyl]propionate (Compound No. V-47)

A solution of Compound No. V-27 (98 mg) in methylene chloride (2 ml) was added with aluminum chloride (81 mg, Ald) and acetyl chloride (60 μl), and stirred for 4 hours. The reaction mixture was added with 1 N hydrochloric acid (2 ml), and extracted with methylene chloride (60 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. V-47, 47 mg).

Example V-48 Synthesis of 3-[3-(3-acetyl-1H-indol-5-yl)-4-cyclopentylmethyloxyphenyl]propionic acid (Compound No. V-48)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 4 hours, Compound No. V-47 (45 mg) and 2 N aqueous sodium hydroxide (110 μl) were reacted and treated to obtain the title compound (Compound No. V-48, 44 mg).

Example V-50 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(3-methyl-1H-indol-5-yl)phenyl]propionate (Compound No. V-50)

According to the procedure described in the synthesis method of Intermediate 95 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1), 5-bromo-3-methylindole (1.63 g) obtainable from 5-bromoindole (TCI) by a known method described in a publication (Wayland, E. N., J. Org. Chem, 1967, vol. 32, p. 828) was reacted with 30% potassium hydride (1.08 g), a 1.7 M solution of t-butyllithium in pentane (9.7 ml) and (^(i)PrO)₃B (3.75 ml) and treated to obtain crude 3-methyl-5-indoleboronic acid. This compound was reacted with Compound No. A-1 (803 mg), 2 M aqueous sodium carbonate (2 ml) and (Ph₃P)₄Pd (241 mg) and treated to obtain the title compound (Compound No. V-50, 552 mg).

Example V-51 Synthesis of 3-[4-cyclopentylmethyloxy-3-(3-methyl-1H-indol-5-yl)phenyl]propionic acid (Compound No. V-51)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. V-50 (130 mg) and 2 N aqueous sodium hydroxide (370 μl) were reacted and treated to obtain the title compound (Compound No. V-51, 127 mg).

Example V-54 Synthesis of 4-bromo-1H-indazole (Intermediate 69)

According to a known method described in a publication (Schumann, P. et al., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1153), the title compound (Intermediate 69, 1.68 g) was obtained from commercially available 3-bromotoluidine (4.51 g, Ald).

Synthesis of methyl 3-[4-cyclopentyloxy-3-(1H-indazol-4-yl)phenyl]propionate (Compound No. V-54)

According to the procedure described in the synthesis method of Compound No. V-22 provided that the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1), Compound No. A-5 (328 mg), bis(pinacolate)diboron (281 mg), PdCl₂(dppf) (61 mg) and potassium acetate (303 mg) were reacted at 80° C. for 4 hours, and then this reaction mixture was added with Intermediate 105 (161 mg), PdCl₂(dppf) (64 mg) and 2 M aqueous sodium carbonate (1.5 ml), reacted at 80° C. for 9 hours and treated to obtain the title compound (Compound No. V-54, 111 mg).

Example V-55 Synthesis of 3-[4-cyclopentyloxy-3-(1H-indazol-4-yl)phenyl]propionic acid (Compound No. V-55)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. V-54 (108 mg) and 2 N aqueous sodium hydroxide (400 μl) were reacted and treated to obtain the title compound (Compound No. V-55, 99 mg).

Example V-57 Synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylnitrobenzene (Intermediate 70)

According to the procedure described in the synthesis method of Compound No. V-22,5-bromo-2-nitrotoluene (4.30 g) synthesized by nitrating 3-bromotoluene (WAKO) by a known method, bis(pinacolate)diboron (5.59 g), PdCl₂(dppf) (440 mg) and potassium acetate (6.09 g) were heated with stirring at 80° C. for 3 hours under argon gas atmosphere. The reaction mixture was added with ethyl acetate (300 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (Intermediate 70, 4.21 g).

Synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylaniline (Intermediate 71)

According to the procedure described in the synthesis method of Compound No. Q-2 with the modification that the reaction was carried out for 30 minutes, Intermediate 70 (4.20 g) and platinum oxide (50 mg) were added, then reacted and treated under hydrogen atmosphere to obtain the title compound (Intermediate 71, 2.81 g).

Synthesis of methyl 3-(4′-amino-6-cyclopentyloxy-3′-methylbiphenyl-3-yl)propionate (Intermediate 72)

According to the procedure described in the synthesis method of Compound No. C-1 with the modifications that the reaction was carried out for 15.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=6:1), Compound No. A-5 (701 mg), Intermediate 71 (604 mg), 2 M aqueous sodium carbonate (1.8 ml), and (Ph₃P)₄Pd (182 mg) were reacted and treated to obtain the title compound (Intermediate 72, 762 mg).

Synthesis of methyl 3-[4-cyclopentyloxy-3-(1H-indazol-5-yl)phenyl]propionate (Compound No. V-57)

A solution of Intermediate 72 (760 mg) in acetic acid (4 ml) was added with an aqueous solution (0.7 ml) of sodium nitrite (156 mg) under ice cooling, and stirred for 30 minutes. This reaction mixture was added with urea (350 mg), warmed to room temperature, stirred for 30 minutes, then added with toluene (8 ml) and water (4 ml), and further stirred for 60 hours. The reaction mixture was extracted with toluene (50 ml×2). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. V-57, 411 mg).

Example V-58 Synthesis of 3-[4-cyclopentyloxy-3-(1H-indazol-5-yl)phenyl]propionic acid (Compound No. V-58)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2.5 hours, Compound No. V-57 (86 mg) and 2 N aqueous sodium hydroxide (250 μl) were reacted and treated to obtain the title compound (Compound No. V-58, 82 mg).

Example V-66 Synthesis of 5-bromo-3-methyl-1H-indazole (Intermediate 73)

According to the procedure described in the synthesis method of Compound No. V-57 provided that the reaction was carried out for 121 hours, 4-bromo-2-ethylaniline (5.01 g, LANC) and sodium nitrite (1.918 g) were reacted and treated to obtain the title compound (Intermediate 73, 3.30 g).

Synthesis of methyl 3-[4-cyclopentyloxy-3-(3-methyl-1H-indazol-5-yl)phenyl]propionate (Compound No. V-66)

According to the procedure described in the synthesis method of Compound No. V-22 provided that the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:2), Compound No. A-5 (434 mg), bis(pinacolate)diboron (367 mg), PdCl₂(dppf) (101 mg), and potassium acetate (339 mg) were reacted at 80° C. for 4 hours, and then this reaction mixture was added with Intermediate 108 (273 mg), PdCl₂(dppf) (104 mg) and 2 M aqueous sodium carbonate (1.1 ml), reacted at 80° C. for 18 hours and treated to obtain the title compound (Compound No. V-66, 98 mg).

Example V-67 Synthesis of 3-[4-cyclopentyloxy-3-(3-methyl-1H-indazol-5-yl)phenyl]propionic acid (Compound No. V-67)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. V-66 (97 mg) and 2 N aqueous sodium hydroxide (400 μl) were reacted and treated to obtain the title compound (Compound No. V-67, 54 mg).

Example V-68 Synthesis of methyl 3-[4-cyclopentyloxy-3-(1,3-dimethyl-1H-indazol-5-yl)phenyl]propionate (Compound No. V-68)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 16 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=3:1), Compound No. V-66 (112 mg), 60% sodium hydride (24 mg) and methyl iodide (95 μl) were reacted and treated to obtain the title compound (Intermediate 110, 45 mg).

Example V-69 Synthesis of 3-[4-cyclopentyloxy-3-(1,3-dimethyl-1H-indazol-5-yl)phenyl]propionic acid (Compound No. V-69)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. V-68 (45 mg) and 2 N aqueous sodium hydroxide (120 μl) were reacted and treated to obtain the title compound (Compound No. V-69, 42 mg).

Example V-73 Synthesis of methyl 3-[3-(benzo[b]thiophen-5-yl)-4-cyclopentylmethyloxyphenyl]propionate (Compound No. V-73)

According to the procedure described in the synthesis method of Compound No. V-22 provided that the purification was performed by column chromatography (Quad, hexane ethyl acetate=10:1), Compound No. A-1 (371 mg), bis(pinacolate)diboron (294 mg), PdCl₂(dppf) (67 mg) and potassium acetate (308 mg) were reacted at 80° C. for 10 hours, and then this reaction mixture was added with 5-bromobenzo[b]thiophene (301.4 mg) obtainable from 4-bromothiophenol (TCI) by a known method described in a publication (Seed, A. J., J. Mater. Chem., 2000, vol. 10, p. 2069), PdCl₂(dppf) (65 mg) and 2 M aqueous sodium carbonate (0.9 ml), reacted at 80° C. for 16 hours and treated to obtain the title compound (Compound No. V-73, 97 mg).

Example V-74 Synthesis of 3-[3-(benzo[b]thiophen-5-yl)-4-cyclopentylmethyloxyphenyl]propionic acid (Compound No. V-74)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. V-73 (95 mg) and 2 N aqueous sodium hydroxide (250 μl) were reacted and treated to obtain the title compound (Compound No. V-74, 93 mg).

Example V-77 Synthesis of (3-bromophenyl)thiourea (Intermediate 74)

A solution of 3-bromoaniline (10.89 ml, TCI) in 20% aqueous hydrochloric acid (18.2 ml) was added with ammonium thiocyanate (8.02 g, WAKO) and sodium hydrogensulfite (701 mg, WAKO), and stirred at 100° C. for 22 hours. The reaction mixture was added with chloroform (20 ml) for extraction, and the organic layer was dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 74, 4.45 g).

Synthesis of 2-amino-5-bromobenzothiazole (Intermediate 75)

A solution of Intermediate 74 (1.29 g) in chloroform (12 ml) was added dropwise with a solution of bromine (272 μl, WAKO) in chloroform (1.5 ml), refluxed by heating for 2.5 hours, and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, neutralized with 5% aqueous ammonia, and then added with water (50 ml) and methylene chloride (150 ml) for extraction. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 75, 609 mg).

Synthesis of methyl 3-[3-(2-aminobenzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]propionate (Compound No. V-77)

A solution of Intermediate 75 (459.1 mg) in anhydrous THF (30 ml) was added with N,N,N′,N′-tetramethylethylenediamine (1.51 ml, WAKO), cooled to −78° C. under argon gas atmosphere, then added dropwise with a 1.62 M solution of t-butyllithium in pentane (7.06 ml), and stirred for 30 minutes. The reaction mixture was added dropwise with (^(i)PrO)₃B (2.77 ml), stirred for 30 minutes, then warmed to room temperature, and further stirred for 1.5 hours. The reaction mixture was added with 0.5 M aqueous sulfuric acid (7.5 ml) and extracted with diethyl ether (50 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 2-amino-5-benzothiazoleboronic acid. This compound was reacted with Compound No. A-1 (344 mg), 2 M aqueous sodium carbonate (4.5 ml) and (Ph₃P)₄Pd (179 mg) and treated according to the procedure described in the synthesis method of Compound No. V-3 with the modifications that the reaction was carried out for 12 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (Compound No. V-77, 76 mg).

Example V-78 Synthesis of 3-[3-(2-aminobenzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]propionic acid (Compound No. V-78)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2.5 hours, Compound No. V-77 (77 mg) and 2 N aqueous sodium hydroxide (380 μl) were reacted and treated to obtain the title compound (Compound No. V-78, 69 mg).

Example V-79 Synthesis of ethyl 3-[3-(benzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]propionate (Compound No. V-79)

A solution of Compound No. V-77 (215 mg) in acetonitrile (10 ml) was added with 30% aqueous hypophosphorous acid (3 ml, WAKO), cooled to 0° C., added dropwise with an aqueous solution (1 ml) of sodium nitrite (187 mg), stirred for 30 minutes, then warmed to room temperature, and further stirred for 20 hours. The reaction mixture was poured into water (50 ml), neutralized by addition of 2 N aqueous sodium hydroxide, and added with ethyl acetate (90 ml×3) for extraction. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 10:1) to obtain the title compound (Compound No. V-79, 78 mg).

Example V-80 Synthesis of 3-[3-(benzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]propionic acid (Compound No. V-80)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours, Compound No. V-79 (75 mg) and 2 N aqueous sodium hydroxide (500 μl) were reacted and treated to obtain the title compound (Compound No. V-80, 66 mg).

Example V-81 Synthesis of methyl 3-[4-cyclopentylmethyloxy-3-(2-methylbenzothiazol-5-yl)phenyl]propionate (Compound No. V-81)

According to the procedure described in the synthesis method of Compound No. V-13 with the modifications that the reaction was carried out for 13 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=5:1), crude 2-methyl-5-benzothiazoleboronic acid prepared from 5-bromo-2-methylbenzothiazole (684 mg, TCI), a 1.7 M solution of t-butyllithium in pentane (7.06 ml) and (^(i)PrO)₃B (3.46 ml), Compound No. A-1 (515 mg), 2 M aqueous sodium carbonate (6.5 ml) and (Ph₃P)₄Pd (258 mg) were reacted and treated to obtain the title compound (Compound No. V-81, 240 mg).

Example V-82 Synthesis of 3-[4-cyclopentylmethyloxy-3-(2-methylbenzothiazol-5-yl)phenyl]propionic acid (Compound No. V-82)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 4 hours, Compound No. V-81 (227 mg) and 2 N aqueous sodium hydroxide (1.11 ml) were reacted and treated to obtain the title compound (Compound No. V-82, 132 mg).

Example V-83 Synthesis of ethyl 3-{4-cyclopentylmethyloxy-3-[2-(N,N-dimethylamino)benzothiazol-6-yl]phenyl}propionate (Compound No. V-83)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 4 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=7:1), Compound No. V-77 (155 mg), 60% sodium hydride (16 mg) and methyl iodide (68.5 μl) were reacted and treated to obtain the title compound (Compound No. V-83, 48 mg).

Example V-84 Synthesis of 3-{4-cyclopentylmethyloxy-3-[2-(N,N-dimethylamino)benzothiazol-6-yl]phenyl}propionic acid (Compound No. V-84)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 3 hours, Compound No. V-83 (47 mg) and 2 N aqueous sodium hydroxide (200 μl) were reacted and treated to obtain the title compound (Compound No. V-84, 35 mg).

Example V-88 Synthesis of ethyl 3-[3-(2-bromobenzothiazol-6-yl)-4-cyclohexylmethyloxyphenyl]propionate (Intermediate 76)

A solution obtained beforehand by adding t-butyl nitrite (178 μl, TCI) and copper(I) bromide (241 mg, WAKO) to acetonitrile (10 ml) and mixing them was added dropwise with a solution of Compound No. V-83 (381 mg) in acetonitrile (5 ml) and stirred at room temperature for 1.5 hours. The solvent of the reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 76, 341 mg).

Synthesis of 3-[4-cyclopentylmethyloxy-3-(2-methoxybenzothiazol-6-yl)phenyl]propionic acid (Compound No. V-88)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 18 hours, Intermediate 76 (169 mg) and 2 N aqueous sodium hydroxide (500 μl) were reacted and treated to obtain the title compound (Compound No. V-88, 114 mg).

Example V-89 Synthesis of 3-[4-cyclopentylmethyloxy-3-(2-oxo-2,3-dihydrobenzothiazol-6-yl)phenyl]propionic acid (Compound No. V-64)

A solution of Intermediate 76 (202 mg) in ethanol (8 ml) was added with 5 N aqueous hydrochloric acid (1.5 ml), and stirred at 80° C. for 18.5 hours. The reaction mixture was concentrated under reduced pressure, and added with water (20 ml) and ethyl acetate (80 ml) for extraction. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was added with 2 N aqueous sodium hydroxide (1.0 ml), reacted and treated according to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours to obtain the title compound (Compound No. V-89, 250 mg).

Example V-91 Synthesis of 3-[4-cyclopentylmethyloxy-3-(2-thioxo-2,3-dihydrobenzothiazol-6-yl)phenyl]propionic acid (Compound No. V-91)

A solution obtained beforehand by adding thiourea (52 mg, WAKO) to 1 M sulfuric acid (5 ml) and mixing them was added with a solution of Intermediate 76 (101 mg) in acetonitrile (5 ml), and stirred at 90° C. for 20 hours. The reaction mixture was poured into water (20 ml), neutralized by addition of 1 N aqueous sodium hydroxide under ice cooling, and then extracted with ethyl acetate (80 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, methylene chloride:ethanol=30:1) to obtain the title compound (Compound No. V-91, 46 mg).

Synthesis examples for compounds used for preparation of the compounds mentioned in the examples are shown below.

Syntheses of 4-bromo-1-methyl-1H-indazole (Intermediate 77) and 4-bromo-2-methyl-2H-indazole (Intermediate 78)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 8 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 69 (600 mg), 60% sodium hydride (191 mg), and methyl iodide (379 μl) were reacted and treated to obtain the title compounds (Intermediate 119, 432 mg and Intermediate 120, 164 mg).

Synthesis of 5-bromo-1H-indazole (Intermediate 79)

The title compound (Intermediate 121, 0.91 g) was obtained from commercially available 4-bromotoluidine (3.33 g, Ald) by a method known from the aforementioned literature (Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1153).

Syntheses of 5-bromo-1-methyl-1H-indazole (Intermediate 80) and 5-bromo-2-methyl-2H-indazole (Intermediate 81)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 4.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 79 (300 mg), 60% sodium hydride (80 mg), and methyl iodide (161 μl) were reacted and treated to obtain the title compounds (Intermediate 80, 201 mg and Intermediate 81, 87 mg).

Synthesis of 1-methyl-1H-indazole-5-boronic acid (Intermediate 82)

According to the procedure described in the synthesis method of Compound No. V-3, Intermediate 80 (1.69 g), a 1.6 M solution of n-butyllithium in hexane (7.50 ml) and (^(i)PrO)₃B (3.23 ml) were reacted and treated to obtain the title compound (Intermediate 82, 1.39 g).

Syntheses of 5-bromo-1-ethyl-1H-indazole (Intermediate 83) and 5-bromo-2-ethyl-2H-indazole (Intermediate 84)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 79 (420 mg), 60% sodium hydride (111 mg), and ethyl iodide (375 μl) were reacted and treated to obtain the title compounds (Intermediate 83, 250 mg and Intermediate 84, 127 mg).

Synthesis of 6-bromo-1H-indazole (Intermediate 85)

The title compound was obtained from commercially available 5-bromotoluidine (3.33 g, Ald) by the method known from the aforementioned literature (Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1153) to obtain the title compound (Intermediate 85, 0.42 g).

Syntheses of 6-bromo-1-methyl-1H-indazole (Intermediate 86) and 6-bromo-2-methyl-2H-indazole (Intermediate 87)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 2.5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=5:1), Intermediate 85 (277 mg), 60% sodium hydride (86 mg), and methyl iodide (175 μl) were reacted and treated to obtain the title compounds (Intermediate 86, 196 mg and Intermediate 87, 89 mg).

Synthesis of 5-bromo-2-t-butylthiobenzaldehyde (Intermediate 88)

A solution of 5-bromo-2-fluorobenzaldehyde (4.06 g, Avocado) in 2-propanol (20 ml) was added with 2-methyl-2-propanethiol (2.26 ml, Ald) and potassium carbonate (3.04 g), and heated with stirring for 18 hours. The reaction mixture was cooled to room temperature, then poured into water (50 ml), and extracted with chloroform (75 ml×3). The organic layer was washed twice with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=20:1) to obtain the title compound (Intermediate 88, 754 mg).

Synthesis of 5-bromobenzo[d]isothiazole (Intermediate 89)

A solution obtained beforehand by mixing 2 N aqueous sodium hydroxide (2.19 ml) in an aqueous solution (5 ml) of hydroxylamine hydrochloride (308 mg, WAKO) was added dropwise to a solution of Intermediate 88 (401 mg) in ethanol (5 ml) at room temperature over 15 minutes. The reaction mixture was refluxed by heating for further 2 hours, then cooled to room temperature, poured into water (30 ml), and extracted with ethyl acetate (100 ml×3). The organic layer was washed successively with aqueous saturated ammonium chloride aqueous, saturated aqueous sodium hydrogencarbonate, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was added with polyphosphoric acid (21.4 g), and heated with stirring at 100° C. for 2 hours. The reaction mixture was poured into ice water (100 ml), neutralized with 5 N aqueous sodium hydroxide under ice cooling, and then extracted with ethyl acetate (100 ml×3). The organic layer was washed twice with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=20:1) to obtain the title compound (Intermediate 89, 143 mg).

Synthesis of 5-bromobenzo[c]isothiazole (Intermediate 90)

A solution of methanesulfonamide (5.34 g, TCI) in dehydrated benzene (9 ml) was added with thionyl chloride (6.0 ml) under ice cooling, and refluxed by heating for 24 hours. The reaction mixture was concentrated under reduced pressure, and a solution of the residue in dehydrated benzene (4 ml) was added dropwise to a solution of 4-bromotoluidine (1.49 g) in dehydrated benzene (40 ml) under ice cooling. This mixture was added dropwise with a solution of pyridine (0.97 ml) in dehydrated benzene (4 ml) under ice cooling, and refluxed by heating for 80 hours under argon gas atmosphere. The reaction mixture was cooled to room temperature, poured into water (100 ml), and extracted with chloroform (100 ml×3). The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 90, 618 mg).

Synthesis of 6-bromoimidazo[1,2-a]pyridine (Intermediate 91)

The title compound (Intermediate 91, 3.36 g) was obtained from commercially available bromoacetaldehyde-diethylacetal (4.7 ml, WAKO) and 2-amino-5-bromopyridine (4.32 g, Ald) by a known method described in a publication (Yamanaka, M. et al., Chem. Pharm. Bull., 1991, vol. 39, p. 1556).

Synthesis of 5-bromo-1H-pyrrolo[2,3-b]pyridine (Intermediate 92)

The title compound (Intermediate 92, 182 mg) was obtained from commercially available 1H-pyrrolo[2,3-b]pyridine (1.3 g, TCI) by a known method described in a publication (Mazeas, D. et al, Heterocycles, 1999, vol. 50, p. 1065).

Synthesis of 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 93)

According to the procedure described in the synthesis method of Compound No. V-29 with the modifications that the reaction was carried out for 2 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=15:1), Intermediate 92 (98 mg), 60% sodium hydride (33 mg), and methyl iodide (53 μl) were reacted and treated to obtain the title compound (Intermediate 93, 88 mg).

Synthesis of 6-bromoisoquinoline (Intermediate 94)

The title compound (Intermediate 94, 1.46 g) was obtained from commercially available 4-bromobenzaldehyde (15.0 g, WAKO) by a known method described in a publication (Nerenz, H. et al., J. Chem. Soc. Perkin Trans. 2, 1998, p. 437].

Synthesis of 6-bromo-2H-isoquinolin-1-one (Intermediate 95)

A solution of Intermediate 94 (1.04 g) in methylene chloride (3 ml) was added with a solution of 3-chloroperbenzoic acid (2.16 g) in methylene chloride (3 ml), and stirred for 20 hours. The reaction mixture was added with methylene chloride (200 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. A solution of the residue in acetic anhydride (10 ml) was refluxed by heating for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was added with 2.5 N aqueous sodium hydroxide (20 ml), and stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature, and neutralized with 5 N aqueous hydrochloric acid under ice cooling to obtain the precipitated title compound (Intermediate 95, 623 mg).

Examples V-1 to V-115

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-V-1 to Table-V-3.

TABLE V-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass V-1 cHexMeO Et H 1-Nap V-1 V-2 cHexMeO H H 1-Nap V-2 C 375 (M⁺ + 1) V-3 cPenMeO Me H 6OH-2-Nap V-3 V-4 cPenMeO H H 6OH-2-Nap V-4 V-5 cPenMeO Me H 5OH-2-Nap V-5 V-6 cPenMeO H H 5OH-2-Nap V-6 V-7 cPenMeO Me H 7OH-2-Nap V-7 V-8 cPenMeO H H 7OH-2-Nap V-8 V-9 cPenMeO Me H 6OMe-2-Nap V-1 V-10 cPenMeO H H 6OMe2-Nap V-2 C 418(M⁺) V-11 cPenMeO Me H 6(OCH₂CONMe₂)-2-Nap V-11 V-12 cPenMeO H H 6(OCH₂CONMe₂)-2-Nap V-12 V-13 cPenMeO Me H 6NH₂-2-Nap V-13 V-14 cPenMeO H H 6NH₂-2-Nap V-14 V-15 cPenMeO H H 6(NMe₂)-2-Nap V-13, V-14 C 418(M⁺ + 1) V-16 cPenMeO H H 6(NHCOCH₂OH)-2-Nap V-16 V-17 cPenMeO H H 6(NHCO-2-Furan)-2-Nap V-16 C 484(M⁺ + 1) V-18 cPenMeO Me H 6(NHSO₂Me)2-Nap V-18 V-19 cPenMeO H H 6(NHSO₂Me)2-Nap V-19 V-20 cPenMeO Me H 6(NHSO₂-NMe₂)-2-Nap V-20 V-21 cPenMeO H H 6(NHSO₂-NMe₂)-2-Nap V-21 V-22 cPenMeO Me H 6(NHSO₂-NH₂)-2-Nap V-22 V-23 cPenMeO H H 6(NHSO₂-NH₂)-2-Nap V-23 V-24 cPenMeO H H 6(SO₂Me)-2-Nap V-22, V-23 C 452(M⁺) V-25 cPenMeO H H 6(SO₂NH₂)-2-Nap V-22, V-23 C 453(M⁺) V-26 cPenMeO H H 6(SO₂NHMe)-2-Nap V-22, V-23 C 468(M⁺ + 1) V-27 cPenO Me H 5-Ind V-27 V-28 cPenO H H 5-Ind V-28 V-29 cPenO Me H 1Me-5-Ind V-29 V-30 cPenO H H 1Me-5-Ind V-30 V-31 cPenMeO Me H 4-Ind V-31 V-32 cPenMeO H H 4-Ind V-32 V-33 cPenMeO Me H 1Me-4-Ind V-33 V-34 cPenMeO H H 1Me-4-Ind V-34 V-35 cPenMeO H H 6-Ind V-31, V-32 C 377(M⁺) V-36 cPenMeO H H 1-Me-6-Ind V-33, V-34 V-37 cPenMeO H H 2-Ind V-31, V-32 A 535 364(M⁺ + 1) V-38 cPenMeO H H 1Me-2-Ind V-29, V-30 V-39 cPenMeO H H 3-Ind V-31, V-32 V-40 cPenMeO H H 1Me-3-Ind V-29, V-30 A 4.75 363(M⁺ + 1) V-41 cPenMeO H H 1iPr-5-Ind V-29, V-30 C 405(M⁺) V-42 cPenMeO H H 1cPen-5-Ind V-29, V-30 C 431(M⁺) V-43 cPenMeO H H 1-(2OHEt)-5-Ind V-43 V-44 cPenMeO Me H 3CHO-5-Ind V-44 V-45 cPenMeO H H 3CHO-5-Ind V-45 V-46 cPenMeO H H 3CHO,1Me-5-Ind V-29, V-30 C 406(M⁺ + 1) V-47 cPenMeO Me H 3Ac-5-Ind V-47 V-48 cPenMeO H H 3Ac-5-Ind V-48 V-49 cPenMeO H H 3Ac,1Me-5-Ind V-29, V-30 C 420(M⁺ + 1) V-50 cPenMeO Me H 3Me-5-Ind V-50 V-51 cPenMeO H H 3Me-5-Ind V-51 V-52 cPenMeO H H 1,3DMe-5Ind V-29, V-30 C 391(M⁺) V-53 cPenMeO H H 1,2,3triMe-5Ind V-22, V-29, V-30 C 405(M⁺) V-54 cPenO Me H 4-1HIdz V-54 V-55 cPenO H H 4-1HIdz V-55 V-56 cPenO H H 1Me-4-1HIdz V-29, V-30 V-57 cPenO Me H 5-1HIdz V-57 V-58 cPenO H H 5-1HIdz V-58 V-59 cPenO H H 1Me-5-1HIdz V-29, V-30 V-60 cPenO H H 1Et-5-1HIdz V-29, V-30 V-61 cPenO H H 1Pr-5-1HIdz V-29, V-30 V-62 cPenO H H 2Me-5-2HIdz V-29, V-30 V-63 cPenMeO H H 6-1HIdz V-57, V-58 V-64 cPenMeO H H 1Me-6-1HIdz V-29, V-30 V-65 cPenMeO H H 1Et-5-1HIdz V-29, V-30 V-66 cPenO Me H 3Me-5-1HIdz V-66 V-67 cPenO H H 3Me-5-1HIdz V-67 V-68 cPenO Me H 1,3DMe-5-1HIdz V-68 V-68 cPenO H H 1,3DMe-5-1HIdz V-69 V-69 cPenO H H 3(CHO)-5-1HIdz V-22, V-23 V-70 cPenO H H 3(CHO),1Me-5-1HIdz V-22, V-23 A 4.38 365(M⁺ + 1) V-71 cPenO H H 3OH-5-1HIdz V-22, V-23 V-72 cPenO H H 3OH,1Me-5-1HIdz V-22, V-23 A 3.71 381(M⁺ + 1) V-73 cPenMeO Me H 5-BT V-73 V-74 cPenMeO H H 5-BT V-74 V-75 cPenMeO H H 5-BF V-22, V-23 C 378(M⁺) V-76 cPenMeO H H 2,3DMe-5-BF V-22, V-23 C 406(M⁺) V-77 cPenMeO Me H 5-2ABzt V-77 V-78 cPenMeO H H 5-2ABzt V-78 V-79 cPenMeO Et H 5-Bzt V-79 V-80 cPenMeO H H 5-Bzt V-80 V-81 cPenMeO Me H 2Me-5-Bzt V-81 V-82 cPenMeO H H 2Me-5-Bzt V-82 V-83 cPenMeO Et H 2,2DMe-5-2ABzt V-83 V-84 cPenMeO H H 2,2DMe-5-2ABzt V-84 V-85 cPenMeO H H 6-2ABzt V-77, V-78 C 397(M⁺ + 1) V-86 cPenMeO H H 6-Bzt V-79, V-80 C 453(M⁺ + 1) V-87 cPenMeO H H 2Me-6-Bzt V-81,V-82 C 410(M⁺ + 1) V-88 cPenMeO H H

V-88 V-89 cPenMeO H H

V-89 V-90 cPenMeO H H

V-29, V-30 C 412(M⁺ + 1) V-91 cPenMeO H H

V-91 C 414(M⁺ + 1) V-92 cPenMeO H H

V-29, V-30 C 425(M⁺ + 1) V-93 cPenO H H

V-22, V-23 B 3.87 368(M⁺ + 1) V-94 cPenO H H

V-22, V-23 B 3.58 368(M⁺ + 1) V-95 cPenO H H

V-22, V-23 A 2.57 315(M⁺ + 1) V-96 cPenO H H

V-22, V-23 A 3.84 351(M⁺ + 1) V-97 cPenO H H

V-29, V-30 A 4.28 365(M⁺ + 1) V-98 cPenMeO H H 3-Qu V-22, V-23 C 376(M⁺ + 1) V-99 cPenMeO H H 6-Qu V-22, V-23 C 376(M⁺ + 1) V-100 cPenO H H 6-IQ V-22, V-23 A 2.15 452(M⁺ + 1) V-101 cPenO H H

V-22, V-23 A 3.74 378(M⁺ + 1) V-102 cPenMeO H H

V-22, V-23 C 378(M⁺ + 1) V-103 cHexMeO Et H

V-33 C 406(M⁺) V-104 cHexMeO H H

V-34 C 378(M⁺ + 1) V-105 cHexMeO Et H

V-33 C 422(M⁺) V-106 cHexMeO H H

V-34 C 394(M⁺) V-107 cHexMeO H H

V-22, V-23 C 455(M⁺ + 1) V-108 cHexMeO H H

V-22, V-23 C 495(M⁺ + 1) V-109 cHexMeO H H

V-22, V-23 C 487(M⁺ + 1) V-110 cPenO H H 3(COOH),1Me-7-1HIdz V-22, V-23 A 3.99 409(M⁺ + 1) V-111 cPenO H H 3(COOH),1Me-5-1HIdz V-22, V-23 A 3.75 409(M⁺ + 1) V-112 cPenO H H 3(COOH),2Me-5-2HIdz V-22, V-23 A 3.96 409(M⁺ + 1) V-113 cPenO H H 3(COOH),2Me-7-2HIdz V-22, V-23 A 3.80 409(M⁺ + 1) V-114 cPenO H H 3(COOH)-7-1HIdz V-22, V-23 A 3.66 395(M⁺ + 1) V-115 cPenO H H 3(COOH)-5-1HIdz V-22, V-23 A 3.49 395(M⁺ + 1)

Examples W-1 to W-25 Synthesis of 6-bromocinnoline (Intermediate 96)

The title compound (Intermediate 96, 134 mg) was obtained from commercially available 4-bromo-2-iodoaniline (711 mg, Ald) by a method known from literature (Kimball, D. et al., Organic Letter, 2000, p. 3825).

Synthesis of 7-bromoquinazoline (Intermediate 97)

The title compound (Intermediate 97, 921 mg) was obtained from commercially available quinazoline (2.11 g, WAKO) by a known method described in a publication (Dalby, B. et al., Synthesis, 2002, p. 83).

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-W-1 and Table-W-2.

TABLE W-1

LCMS Exp. RxO Y Zx AR Syn method RTime Mass W-1 cPenMeO H H

V-22, V-23 C 366(M⁺ + 1) W-2 cPenMeO H H

V-22, V-23 C 383(M⁺ + 1) W-3 cPenMeO H H

V-22, V-23 C 365(M⁺ + 1) W-4 cPenMeO H H

V-22, V-23 C 380(M⁺ + 1) W-5 cPenMeO H H

V-22, V-23 C 366(M⁺ + 1) W-6 cPenMeO H H

V-22, V-23 C 380(M⁺ + 1) W-7 cPenMeO H H

V-22, V-23 C 381(M⁺ + 1) W-8 cPenMeO H H

V-22, V-23 C 398(M⁺ + 1) W-9 cPenMeO H H

V-22, V-23 C 382(M⁺ + 1) W-10 cPenMeO H H

V-22, V-23 C 366(M⁺ + 1) W-11 cPenMeO H H

V-22, V-23 C 377(M⁺ + 1) W-12 cPenO H H

V-22, V-23 A 3.97 363(M⁺ + 1) W-13 cPenO H H

V-22, V-23 A 4.06 363(M⁺ + 1) W-14 cPenMeO H H

V-22, V-23 C 380(M⁺ + 1) W-15 cPenO H H

V-22, V-23 C 355(M⁺ + 1) W-16 cPenMeO H H

V-22, V-23 C 397(M⁺ + 1) W-17 cPenMeO H H

V-22, V-23 C 381(M⁺ + 1) W-18 cPenMeO H H

V-22, V-23 C 380(M⁺ + 1) W-19 cPenMeO H H

V-22, V-23 C 381(M⁺ + 1) W-20 cPenMeO H H

V-22, V-23 C 398(M⁺ + 1) W-21 cPenMeO H H

V-22, V-23 C 382(M⁺ + 1) W-22 cPenO H H

V-22, V-23 C 351(M⁺ + 1) W-23 cPenO H H

V-22, V-23 C 353(M⁺ + 1) W-24 cPenO H H

V-22, V-23 C 353(M⁺ + 1) W-25 cPenO H H

V-22, V-23 C 367(M⁺ + 1)

Example X-1 Synthesis of ethyl 3-[2-cyclopentyloxy-5-(naphthalen-2-yl)phenyl]acrylate (Intermediate 98)

According to the procedure described in the synthesis method of Intermediate 7 provided that the reaction was carried out for 1 hour, Compound No. D-20 (396 mg), ethyl diethylphosphonoacetate (288 μl), and 60% sodium hydride (59 mg) were reacted and treated to obtain the title compound (Intermediate 98, 428 mg).

Synthesis of ethyl 3-[2-cyclohexylmethyloxy-5-(naphthalen-1-yl)phenyl]propionate (Compound No. X-1)

According to the procedure described in the synthesis method of Intermediate B-99 with the modifications that the reaction was carried out at 50° C. for 5 hours, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate=10:1), Intermediate 98 (361 mg) and Raney 2800 nickel (380 mg) were reacted and treated to obtain the title compound (Compound No. X-1, 397 mg).

Example X-2 Synthesis of 3-[2-cyclohexylmethyloxy-5-(naphthalen-1-yl)phenyl]propionic acid (Compound No. X-2)

According to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2.5 hours, Compound No. X-1 (390 mg) and 2 N aqueous sodium hydroxide (1.1 ml) were reacted and treated to obtain the title compound (Compound No. X-2, 338 mg).

Examples X-1 to X-4

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-X-1.

TABLE X-1

RxO AR LCMS Exp. RxO Y positio AR Syn position method RTime Mass X-1 cPenO Et 2 2-Nap X-1 5 X-2 cPenO H 2 2-Nap X-2 5 C 347(M⁺ + 1) X-3 cPenO H 2 1Me-5-Ind X-1, X-2 5 C 350(M⁺ + 1) X-4 cPenO H 2 1Me-5-1HIdz X-1, X-2 5 C 351(M⁺ + 1)

Reference Examples Intermediates Aa-1 to Aa-47 Synthesis of methyl 3-[3-(naphthalen-2-yl)-4-trifluoromethanesulfonylphenyl]-propionate (Intermediate Aa-1)

A solution of Intermediate 41 (4.34 g) in dehydrated pyridine (120 ml) was added with trifluoromethanesulfonic anhydride (2.6 ml, ALD) under ice cooling, then warmed to room temperature, and stirred for 4 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with ethyl acetate (800 ml). The organic layer was washed successively with 1 N hydrochloric acid, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=6:1) to obtain the title compound (Intermediate Aa-1, 4.98 g).

Typical examples of the reaction intermediates including those mentioned above, that can be obtained by reacting and treating corresponding starting compounds according to the synthesis method of Intermediate Aa-1, are shown in Table-Aa-1.

In the column indicated as “Mass” in the table, data of mass spectra measured by fast atom bombardment mass spectrometry (FAB-MS) are shown.

TABLE Aa-1

Exp. AR Mass Aa-1 2-Nap 439 (M⁺ + 1) Aa-2 5-Ind 428 (M⁺ + 1) Aa-3 1Me-5-Ind 442 (M⁺ + 1) Aa-4 5-1HIdz 429 (M⁺ + 1) Aa-5 1Me-5-1HIdz 443 (M⁺ + 1) Aa-6 5-BF 432 (M⁺ + 1) Aa-7 3-Qu 440 (M⁺ + 1) Aa-8 1-Nap 439 (M⁺ + 1) Aa-9 6(MeO)-2-Nap 469 (M⁺ + 1) Aa-10 6(NMe₂)-2-Nap 482 (M⁺ + 1) Aa-11 4-Ind 428 (M⁺ + 1) Aa-12 1Me-4-Ind 442 (M⁺ + 1) Aa-13 6-Ind 428 (M⁺ + 1) Aa-14 1Me-6-Ind 442 (M⁺ + 1) Aa-15 2-Ind 428 (M⁺ + 1) Aa-16 1Me-2-Ind 442 (M⁺ + 1) Aa-17 3-Ind 428 (M⁺ + 1) Aa-18 1Me-3-Ind 442 (M⁺ + 1) Aa-19 1iPr-5-Ind 470 (M⁺ + 1) Aa-20 1cPen-5-Ind 496 (M⁺ + 1) Aa-21 3Me-5-Ind 442 (M⁺ + 1) Aa-22 1,3DMe-5Ind 456 (M⁺ + 1) Aa-23 1,2,3triMe-5Ind 470 (M⁺ + 1) Aa-24 4-1HIdz 429 (M⁺ + 1) Aa-25 1Me-4-1HIdz 443 (M⁺ + 1) Aa-26 5-1HIdz 429 (M⁺ + 1) Aa-27 1Me-5-1HIdz 443 (M⁺ + 1) Aa-28 1Et-5-1HIdz 457 (M⁺ + 1) Aa-29 1Pr-5-1HIdz 471 (M⁺ + 1) Aa-30 2Me-5-2HIdz 443 (M⁺ + 1) Aa-31 6-1HIdz 429 (M⁺ + 1) Aa-32 1Me-6-1HIdz 443 (M⁺ + 1) Aa-33 3Me-5-1HIdz 443 (M⁺ + 1) Aa-34 1,3DMe-5-1HIdz 457 (M⁺ + 1) Aa-35 5-BT 445 (M⁺ + 1) Aa-36 2,3DMe-5-BF 457 (M⁺ + 1) Aa-37 5-2ABzt 461 (M⁺ + 1) Aa-38 5-Bzt 456 (M⁺ + 1) Aa-39 2Me-5-Bzt 460 (M⁺ + 1) Aa-40 2,2DMe-5-2ABzt 489 (M⁺ + 1) Aa-41 6-2ABzt 461 (M⁺ + 1) Aa-42 6-Bzt 456 (M⁺ + 1) Aa-43 2Me-6-Bzt 460 (M⁺ + 1) Aa-44 6-Qu 440 (M⁺ + 1) Aa-45 6-IQ 440 (M⁺ + 1) Aa-46 2-BF 429 (M⁺ + 1) Aa-47 2-BT 445 (M⁺ + 1)

Example Ca-1 Synthesis of methyl 3-[4-(phenyl)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. Ca-1)

Compound No. Aa-1 (138.4 mg, corresponding to the substance mentioned in the column of SM1 in Table-Ca-1 mentioned later), phenylboronic acid (71.3 mg, corresponding to the substance mentioned in the column of SM 2 mentioned in Table-Ca-1 mentioned later), cesium carbonate (254.9 mg), PdCl₂(dppf) (25.6 mg) were added with toluene (600 μl), methanol (1.2 ml), and water (1.2 ml), and stirred at 80° C. for 17 hours under nitrogen atmosphere. The reaction mixture was added with ethyl acetate (30 ml), washed successively with water and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (Compound No. Ca-1, 140.6 mg).

Example Ca-2 Synthesis of 3-[4-phenyl-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. Ca-2)

A solution of Compound Ca-1 (137.7 mg) in methanol (4.0 ml) was added with 2 N aqueous sodium hydroxide (720 μl), and stirred at 60° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, then made acidic with 5% aqueous hydrochloric acid under ice cooling, and extracted with ethyl acetate (50 ml). The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. Ca-2, 108 mg).

Examples Ca-1 to Ca-270 and Examples Cb-1 to Cb-95

Typical examples of the compounds of the present invention including those mentioned in the examples described above, that can be obtained by reacting and treating corresponding starting compounds according to the methods described in Examples Ca-1 and Ca-2, are shown in Table-Ca-1 to Table-Ca-5, Table-Cb-1 and Table-Cb-2.

The substances mentioned in the columns of “SM1” in the tables correspond to reaction intermediates, and those mentioned in the columns of “SM2” in the tables correspond to the boronic acid reagent used in Example Ca-1. The boronic acid reagents shown with the symbols of “BRA (number)” mentioned in the columns of “SM2” are those mentioned in Table-Ba-1 and Table-Ba-2. The regents for which cells of the columns of “Manufacturer” in the tables are blank are synthesized according to a method described in ordinary chemical literatures.

TABLE Ba-1 Reagen Name of reagent Manufacture BRA1 Naphthalene-2-boronic acid TCI BRA2 (1H-Indol-5-yl) boronic acid Frontier BRA3 (1-Methyl-1H-indol-5-yl) boronic acid Frontier BRA4 (1-Ethyl-1H-indol-5-yl) boronic acid BRA5 (1H-Indazol-5-yl) boronic acid BRA6 (1-Methyl-1H-indazol-5-yl) boronic acid BRA7 (1-Ethyl-1H-indazol-5-yl) boronic acid BRA8 (2-Methyl-2H-indazol-5-yl) boronic acid BRA9 Benzothiazole-6-yl-4,4,5,5-tetramethyl- 1,3,2-dioxaborolan BRA10 Quinoline-3-boronic acid Frontier BRA11 Quinoline-6-yl-4,4,5,5-tetramethyl- Ald 1,3,2-dioxaborolan BRA12 Isoquinoline-6-yl-4,4,5,5-tetramethyl- 1,3,2-dioxaborolan BRA13 Methyl boronic acid Ald BRA14 Phenyl boronic acid Ald BRA15 4-Hydroxyphenyl boronic acid Ald BRA16 Naphthalene-1-boronic acid Ald BRA17 3.5-Bis(trifluoromethyl) phenyl boronic acid TCI BRA18 Benzo[b]furan-2-boronic acid Ald BRA19 4-Methoxypheny boronic acid Ald BRA20 2-Methylpropyl boronic acid Ald BRA21 4-(Dimethylamino) phenyl boronic acid Ald BRA22 4-Fluorophenyl boronic acid TCI BRA23 Cyclopropyl boronic acid BRA24 6-Ethoxynaphthalene-2-boronic acid Ald BRA25 Benzo[b]thiophene-2-boronic acid LANC BRA26 Pyridine-4-boronic acid ALD BRA27 Dibenzofuran-2-boronic acid Ald BRA28 Cyclopentyl boronic acid LANC BRA29 4-Methylphenyl boronic acid Ald BRA30 4-Chlorophenyl boronic acid Ald BRA31 1-n-Butyl boronic acid Ald BRA32 2-Fluorophenyl boronic acid Ald BRA33 3-Fluorophenyl boronic acid Ald BRA34 4-Fluorophenyl boronic acid Ald BRA35 2-Furyl boronic acid Ald BRA36 2-Thienyl boronic acid Ald BRA37 3-Methoxyphenyl boronic acid Ald BRA38 2-Methoxyphenyl boronic acid BRA39 2-(Trifluoromethyl) phenyl boronic acid BRA40 3-(Trifluoromethyl) phenyl boronic acid BRA41 4-(Trifluoromethyl) phenyl boronic acid BRA42 Indan-2-yl-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane BRA43 4-Methylindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA44 5-Methylindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane

TABLE Ba-2 Reagent Name of reagent Manufacture BRA45 4,7-Dimethylindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA46 5,6-Dimethylindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA47 5-Fluoroindan-2-yl-4.4,5,5- tetramethyl-1,3,2-dioxaborolane BRA48 4-Fluoroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA49 4,7-Difluoroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA50 5,6-Difluoroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA51 4-Chloroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA52 5-Chloroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA53 4,7-Dichloroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA54 5,6-Dichloroindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA55 4-Methoxyindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA56 5-Methoxyindan-2-yl-4,4,5,5- tetramethyl-1,3,2-dioxaborolane BRA57 5,6-Dimethoxyindan-2-yl- 4,4,5,5-tetramethyl-1,3,2- BRA58 Cyclohexyl boronic acid Ald BRA59 2-Methylphenyl boronic acid Ald BRA60 3-Methylphenyl boronic acid Ald BRA61 2-Chlorophenyl boronic acid Ald BRA62 3-Chlorophenyl boronic acid Ald BRA63 2,3-Bis(trifluoromethyl) phenyl boronic acid BRA64 2,4-Bis(trifluoromethyl) phenyl boronic acid BRA65 2,5-Bis(trifluoromethyl) phenyl boronic acid BRA66 3,4-Bis(trifluoromethyl) phenyl boronic acid BRA67 3-Furyl boronic acid Ald BRA68 3-Thienyl boronic acid Ald BRA69 Pyridine-2-yl-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane BRA70 Pyridine-3-boronic acid Ald BRA71 2,3-Dimethylphenyl boronic acid Ald BRA72 2,5-Dimethylphenyl boronic acid Ald BRA73 3,5-Dimethylphenyl boronic acid Ald BRA74 2,3-DiChlorophenyl boronic acid Ald BRA75 2,4-DiChlorophenyl boronic acid Ald BRA76 2,5-DiChlorophenyl boronic acid Ald BRA77 2,6-DiChlorophenyl boronic acid Acros BRA78 3,4-DiChlorophenyl boronic acid Ald BRA79 3,5-DiChlorophenyl boronic acid Ald BRA80 2,3-Difluorophenyl boronic acid Ald BRA81 2,4-Difluorophenyl boronic acid Ald BRA82 2,5-Difluorophenyl boronic acid Ald BRA83 2,6-Difluorophenyl boronic acid Ald BRA84 3,4-Difluorophenyl boronic acid Ald BRA85 3,5-Difluorophenyl boronic acid Ald BRA86 2-(Dimethylamino) phenyl boronic acid Digital BRA87 3-(Dimethylamino) phenyl boronic acid Digital BRA88 4-Phenoxy phenyl boronic acid Ald

TABLE Ca-1

LCMS Exp. Rx Y Zx AR SM1 SM2 method RTime Mass Ca-1 Ph Me H 2-Nap Aa-1 BRA14 D N.D Ca-2 Ph H H 2-Nap Ca-1 — C 353 (M⁺ + 1) Ca-3 Ph Me H 5-Ind Aa-2 BRA14 C 356 (M⁺ + 1) Ca-4 Ph H H 5-Ind Ca-3 — C 342 (M⁺ + 1) Ca-5 Ph Me H 1Me-5-Ind Aa-3 BRA14 C 370 (M⁺ + 1) Ca-6 Ph H H 1Me-5-Ind Ca-5 — C 356 (M⁺ + 1) Ca-7 Ph H H 5-1HIdz Aa-4 BRA14 C 343 (M⁺ + 1) Ca-8 Ph Me H 1Me-5-1HIdz Aa-5 BRA14 C 371 (M⁺ + 1) Ca-9 Ph H H 1Me-5-1HIdz Ca-8 — C 357 (M⁺ + 1) Ca-10 Ph H H 5-BF Aa-6 BRA14 C 342 (M⁺ + 1) Ca-11 Ph H H 3-Qu Aa-7 BRA14 C 354 (M⁺ + 1) Ca-12 Ph H H 1-Nap Aa-8 BRA14 C 353 (M⁺ + 1) Ca-13 Ph H H 6(OMe)-2-Nap Aa-9 BRA14 C 383 (M⁺ + 1) Ca-14 Ph H H 6(NMe2)-2-Nap Aa-10 BRA14 C 396 (M⁺ + 1) Ca-15 Ph H H 4-Ind Aa-11 BRA14 C 342 (M⁺ + 1) Ca-16 Ph H H 1Me-4-Ind Aa-12 BRA14 C 356 (M⁺ + 1) Ca-17 Ph H H 6-Ind Aa-13 BRA14 C 342 (M⁺ + 1) Ca-18 Ph H H 1Me-6-Ind Aa-14 BRA14 C 356 (M⁺ + 1) Ca-19 Ph H H 2-Ind Aa-15 BRA14 C 342 (M⁺ + 1) Ca-20 Ph H H 1Me-2-Ind Aa-16 BRA14 C 356 (M⁺ + 1) Ca-21 Ph H H 3-Ind Aa-17 BRA14 C 342 (M⁺ + 1) Ca-22 Ph H H 1Me-3-Ind Aa-18 BRA14 C 356 (M⁺ + 1) Ca-23 Ph H H 1iPr-5-Ind Aa-19 BRA14 C 384 (M⁺ + 1) Ca-24 Ph H H 1cPen-5-Ind Aa-20 BRA14 C 410 (M⁺ + 1) Ca-25 Ph H H 3Me-5-Ind Aa-21 BRA14 C 356 (M⁺ + 1) Ca-26 Ph H H 1,3DMe-5-Ind Aa-22 BRA14 C 370 (M⁺ + 1) Ca-27 Ph H H 1,2,3triMe-5-Ind Aa-23 BRA14 C 384 (M⁺ + 1) Ca-28 Ph H H 4-1HIdz Aa-24 BRA14 C 343 (M⁺ + 1) Ca-29 Ph H H 1Me-4-1HIdz Aa-25 BRA14 C 357 (M⁺ + 1) Ca-30 Ph H H 5-1HIdz Aa-26 BRA14 C 343 (M⁺ + 1) Ca-31 Ph H H 1Me-5-1HIdz Aa-27 BRA14 C 357 (M⁺ + 1) Ca-32 Ph H H 1Et-5-1HIdz Aa-28 BRA14 C 371 (M⁺ + 1) Ca-33 Ph H H 1Pr-5-1HIdz Aa-29 BRA14 C 385 (M⁺ + 1) Ca-34 Ph H H 2Me-5-2HIdz Aa-30 BRA14 C 357 (M⁺ + 1) Ca-35 Ph H H 6-1HIdz Aa-31 BRA14 C 343 (M⁺ + 1) Ca-36 Ph H H 1Me-6-1HIdz Aa-32 BRA14 C 357 (M⁺ + 1) Ca-37 Ph H H 3Me-5-1HIdz Aa-33 BRA14 C 357 (M⁺ + 1) Ca-38 Ph H H 1,3DMe-5-1HIdz Aa-34 BRA14 C 371 (M⁺ + 1) Ca-39 Ph H H 5-BT Aa-35 BRA14 C 359 (M⁺ + 1) Ca-40 Ph H H 2,3DMe-5-BF Aa-36 BRA14 C 387 (M⁺ + 1) Ca-41 Ph H H 5-2ABzt Aa-37 BRA14 C 375 (M⁺ + 1) Ca-42 Ph H H 5-Bzt Aa-38 BRA14 C 360 (M⁺ + 1) Ca-43 Ph H H 2Me-5-Bzt Aa-39 BRA14 C 374 (M⁺ + 1) Ca-44 Ph H H 2,2DMe-5-2ABzt Aa-40 BRA14 C 403 (M⁺ + 1) Ca-45 Ph H H 6-2ABzt Aa-41 BRA14 C 375 (M⁺ + 1) Ca-46 Ph H H 6-Bzt Aa-42 BRA14 C 360 (M⁺ + 1) Ca-47 Ph H H 2Me-6-Bzt Aa-43 BRA14 C 374 (M⁺ + 1) Ca-48 Ph H H 6-Qu Aa-44 BRA14 C 354 (M⁺ + 1) Ca-49 Ph H H 6-IQ Aa-45 BRA14 C 354 (M⁺ + 1) Ca-50 Ph H H 2-BF Aa-46 BRA14 C 342 (M⁺ + 1) Ca-51 Ph H H 2-BT Aa-47 BRA14 C 359 (M⁺ + 1) Ca-52 4MeOPh H H 2-Nap Aa-1 BRA19 C 383 (M⁺ + 1) Ca-53 4MeOPh H H 1Me-5-Ind Aa-3 BRA19 C 386 (M⁺ + 1) Ca-54 4MeOPh H H 5-1HIdz Aa-4 BRA19 C 373 (M⁺ + 1) Ca-55 4MeOPh H H 1Me-5-1HIdz Aa-5 BRA19 C 387 (M⁺ + 1) Ca-56 4MeOPh H H 3-Qu Aa-7 BRA19 C 384 (M⁺ + 1) Ca-57 4MeOPh H H 1Et-5-1HIdz Aa-28 BRA19 C 401 (M⁺ + 1) Ca-58 3MeOPh H H 5-Ind Aa-2 BRA37 C 372 (M⁺ + 1) Ca-59 3MeOPh H H 1Me-5-Ind Aa-3 BRA37 C 386 (M⁺ + 1) Ca-60 3MeOPh H H 5-1HIdz Aa-4 BRA37 C 373 (M⁺ + 1) Ca-61 3MeOPh H H 1Me-5-1HIdz Aa-5 BRA37 C 387 (M⁺ + 1) Ca-62 3MeOPh H H 3-Qu Aa-7 BRA37 C 384 (M⁺ + 1) Ca-63 3MeOPh H H 1Et-5-1HIdz Aa-28 BRA37 C 401 (M⁺ + 1) Ca-64 2MeOPh H H 2-Nap Aa-1 BRA38 C 383 (M⁺ + 1) Ca-65 2MeOPh H H 5-Ind Aa-2 BRA38 C 372 (M⁺ + 1) Ca-66 2MeOPh H H 1Me-5-Ind Aa-3 BRA38 C 386 (M⁺ + 1) Ca-67 2MeOPh H H 5-1HIdz Aa-4 BRA38 C 373 (M⁺ + 1) Ca-68 2MeOPh H H 1Me-5-1HIdz Aa-5 BRA38 C 387 (M⁺ + 1) Ca-69 2MeOPh H H 5-Bzt Aa-38 BRA38 C 390 (M⁺ + 1) Ca-70 2MeOPh H H 3-Qu Aa-7 BRA38 C 384 (M⁺ + 1) Ca-71 2MeOPh H H 1Et-5-1HIdz Aa-28 BRA38 C 401 (M⁺ + 1) Ca-72 2MePh H H 2-Nap Aa-1 BRA59 C 367 (M⁺ + 1) Ca-73 2MePh H H 5-Ind Aa-2 BRA59 C 356 (M⁺ + 1) Ca-74 2MePh H H 1Me-5-Ind Aa-3 BRA59 C 370 (M⁺ + 1) Ca-75 2MePh H H 5-1HIdz Aa-4 BRA59 C 357 (M⁺ + 1) Ca-76 2MePh H H 1Me-5-1HIdz Aa-5 BRA59 C 371 (M⁺ + 1) Ca-77 2MePh H H 5-Bzt Aa-38 BRA59 C 374 (M⁺ + 1) Ca-78 3MePh H H 2-Nap Aa-1 BRA60 C 367 (M⁺ + 1) Ca-79 3MePh H H 5-Ind Aa-2 BRA60 C 356 (M⁺ + 1) Ca-80 3MePh H H 5-1HIdz Aa-4 BRA60 C 357 (M⁺ + 1) Ca-81 3MePh H H 1Me-5-1HIdz Aa-5 BRA60 C 371 (M⁺ + 1) Ca-82 3MePh H H 5-Bzt Aa-38 BRA60 C 374 (M⁺ + 1) Ca-83 3MePh H H 1Et-5-1HIdz Aa-28 BRA60 C 385 (M⁺ + 1) Ca-84 4MePh H H 2-Nap Aa-1 BRA29 C 367 (M⁺ + 1) Ca-85 4MePh H H 5-Ind Aa-2 BRA29 C 356 (M⁺ + 1) Ca-86 4MePh H H 1Me-5-Ind Aa-3 BRA29 C 370 (M⁺ + 1) Ca-87 4MePh H H 5-1HIdz Aa-4 BRA29 C 357 (M⁺ + 1) Ca-88 4MePh H H 1Me-5-1HIdz Aa-5 BRA29 C 371 (M⁺ + 1) Ca-89 4MePh H H 5-Bzt Aa-38 BRA29 C 374 (M⁺ + 1) Ca-90 4MePh H H 3-Qu Aa-7 BRA29 C 368 (M⁺ + 1) Ca-91 4MePh H H 1Et-5-1HIdz Aa-25 BRA29 C 385 (M⁺ + 1) Ca-92 2,3DMePh H H 5-Ind Aa-2 BRA71 C 370 (M⁺ + 1) Ca-93 2,3DMePh H H 1Me-5-Ind Aa-3 BRA71 C 384 (M⁺ + 1) Ca-94 2,3DMePh H H 5-1HIdz Aa-4 BRA71 C 371 (M⁺ + 1) Ca-95 2,3DMePh H H 1Me-5-1HIdz Aa-5 BRA71 C 385 (M⁺ + 1) Ca-96 2,3DMePh H H 1Et-5-1HIdz Aa-28 BRA71 C 399 (M⁺ + 1) Ca-97 2,5DMePh H H 2-Nap Aa-1 BRA72 C 381 (M⁺ + 1) Ca-98 2,5DMePh H H 1Me-5-Ind Aa-3 BRA72 C 384 (M⁺ + 1) Ca-99 2,5DMePh H H 5-1HIdz Aa-4 BRA72 C 371 (M⁺ + 1) Ca-100 2,5DMePh H H 1Me-5-1HIdz Aa-5 BRA72 C 385 (M⁺ + 1) Ca-101 2,5DMePh H H 1Et-5-1HIdz Aa-28 BRA72 C 399 (M⁺ + 1) Ca-102 3,5DMePh H H 2-Nap Aa-1 BRA73 C 381 (M⁺ + 1) Ca-103 3,5DMePh H H 1Me-5-Ind Aa-3 BRA73 C 384 (M⁺ + 1) Ca-104 3,5DMePh H H 1Me-5-1HIdz Aa-5 BRA73 C 385 (M⁺ + 1) Ca-105 2CF₃Ph H H 2-Nap Aa-1 BRA39 C 421 (M⁺ + 1) Ca-106 2CF₃Ph H H 5-Ind Aa-2 BRA39 C 410 (M⁺ + 1) Ca-107 2CF₃Ph H H 1Me-5-1HIdz Aa-5 BRA39 C 425 (M⁺ + 1) Ca-108 2CF₃Ph H H 5-Bzt Aa-38 BRA39 C 428 (M⁺ + 1) Ca-109 2CF₃Ph H H 3-Qu Aa-7 BRA39 C 422 (M⁺ + 1) Ca-110 2CF₃Ph H H 1Et-5-1HIdz Aa-28 BRA39 C 439 (M⁺ + 1) Ca-111 3CF₃Ph H H 2-Nap Aa-1 BRA40 C 421 (M⁺ + 1) Ca-112 3CF₃Ph H H 5-Ind Aa-2 BRA40 C 410 (M⁺ + 1) Ca-113 3CF₃Ph H H 1Me-5-Ind Aa-3 BRA40 C 424 (M⁺ + 1) Ca-114 3CF₃Ph H H 1Me-5-1HIdz Aa-5 BRA40 C 425 (M⁺ + 1) Ca-115 3CF₃Ph H H 5-Bzt Aa-38 BRA40 C 428 (M⁺ + 1) Ca-116 3CF₃Ph H H 3-Qu Aa-7 BRA40 C 422 (M⁺ + 1) Ca-117 4CF₃Ph H H 5-Ind Aa-2 BRA41 C 410 (M⁺ + 1) Ca-118 4CF₃Ph H H 5-1HIdz Aa-4 BRA41 C 411 (M⁺ + 1) Ca-119 4CF₃Ph H H 1Me-5-1HIdz Aa-5 BRA41 C 425 (M⁺ + 1) Ca-120 4CF₃Ph H H 5-Bzt Aa-38 BRA41 C 428 (M⁺ + 1) Ca-121 4CF₃Ph H H 3-Qu Aa-7 BRA41 C 422 (M⁺ + 1) Ca-122 4CF₃Ph H H 1Et-5-1HIdz Aa-28 BRA41 C 439 (M⁺ + 1) Ca-123 2ClPh H H 5-Ind Aa-2 BRA61 C 376 (M⁺ + 1) Ca-124 2ClPh H H 5-1HIdz Aa-4 BRA61 C 377 (M⁺ + 1) Ca-125 2ClPh H H 1Me-5-1HIdz Aa-5 BRA61 C 391 (M⁺ + 1) Ca-126 2ClPh H H 3-Qu Aa-7 BRA61 C 388 (M⁺ + 1) Ca-127 3ClPh H H 2-Nap Aa-1 BRA62 C 387 (M⁺ + 1) Ca-128 3ClPh H H 1Me-5-Ind Aa-3 BRA62 C 390 (M⁺ + 1) Ca-129 3ClPh H H 5-1HIdz Aa-4 BRA62 C 377 (M⁺ + 1) Ca-130 3ClPh H H 1Me-5-1HIdz Aa-5 BRA62 C 391 (M⁺ + 1) Ca-131 3ClPh H H 5-Bzt Aa-38 BRA62 C 394 (M⁺ + 1) Ca-132 4ClPh H H 5-Ind Aa-2 BRA30 C 376 (M⁺ + 1) Ca-133 4ClPh H H 1Me-5-Ind Aa-3 BRA30 C 390 (M⁺ + 1) Ca-134 4ClPh H H 1Me-5-1HIdz Aa-5 BRA30 C 391 (M⁺ + 1) Ca-135 4ClPh H H 5-Bzt Aa-38 BRA30 C 394 (M⁺ + 1) Ca-136 2,3DClPh H H 5-Ind Aa-2 BRA74 C 411 (M⁺ + 1) Ca-137 2,3DClPh H H 1Me-5-Ind Aa-3 BRA74 C 425 (M⁺ + 1) Ca-138 2,3DClPh H H 1Me-5-1HIdz Aa-5 BRA74 C 426 (M⁺ + 1) Ca-139 2,4DClPh H H 5-Ind Aa-2 BRA75 C 411 (M⁺ + 1) Ca-140 2,4DClPh H H 1Me-5-1HIdz Aa-5 BRA75 C 426 (M⁺ + 1) Ca-141 2,4DClPh H H 5-Bzt Aa-38 BRA75 C 429 (M⁺ + 1) Ca-142 2,5DClPh H H 1Me-5-Ind Aa-3 BRA76 C 425 (M⁺ + 1) Ca-143 2,5DClPh H H 1Me-5-1HIdz Aa-5 BRA76 C 426 (M⁺ + 1) Ca-144 2,6DClPh H H 1Me-5-1HIdz Aa-5 BRA77 C 426 (M⁺ + 1) Ca-145 3,4DClPh H H 2-Nap Aa-1 BRA78 C 421 (M⁺ + 1) Ca-146 3,4DClPh H H 5-Ind Aa-2 BRA78 C 411 (M⁺ + 1) Ca-147 3,4DClPh H H 1Me-5-Ind Aa-3 BRA78 C 425 (M⁺ + 1) Ca-148 3,4DClPh H H 1Me-5-1HIdz Aa-5 BRA78 C 426 (M⁺ + 1) Ca-149 3,5DClPh H H 2-Nap Aa-1 BRA79 C 421 (M⁺ + 1) Ca-150 3,5DClPh H H 1Me-5-Ind Aa-3 BRA79 C 425 (M⁺ + 1) Ca-151 3,5DClPh H H 1Me-5-1HIdz Aa-5 BRA79 C 426 (M⁺ + 1) Ca-152 2FPh H H 2-Nap Aa-1 BRA32 C 371 (M⁺ + 1) Ca-153 2FPh H H 1Me-5-Ind Aa-3 BRA32 C 374 (M⁺ + 1) Ca-154 2FPh H H 5-1HIdz Aa-4 BRA32 C 361 (M⁺ + 1) Ca-155 2FPh H H 1Me-5-1HIdz Aa-5 BRA32 C 375 (M⁺ + 1) Ca-156 2FPh H H 5-Bzt Aa-38 BRA32 C 378 (M⁺ + 1) Ca-157 2FPh H H 3-Qu Aa-7 BRA32 C 372 (M⁺ + 1) Ca-158 3FPh H H 5-Ind Aa-2 BRA33 C 360 (M⁺ + 1) Ca-159 3FPh H H 5-1HIdz Aa-4 BRA33 C 361 (M⁺ + 1) Ca-160 3FPh H H 1Me-5-1HIdz Aa-5 BRA33 C 375 (M⁺ + 1) Ca-161 3FPh H H 3-Qu Aa-7 BRA33 C 372 (M⁺ + 1) Ca-162 4FPh H H 2-Nap Aa-1 BRA34 C 371 (M⁺ + 1) Ca-163 4FPh H H 5-Ind Aa-2 BRA34 C 360 (M⁺ + 1) Ca-164 4FPh H H 5-1HIdz Aa-4 BRA34 C 361 (M⁺ + 1) Ca-165 4FPh H H 1Me-5-1HIdz Aa-5 BRA34 C 375 (M⁺ + 1) Ca-166 4FPh H H 3-Qu Aa-7 BRA34 C 372 (M⁺ + 1) Ca-167 2,3DFPh H H 2-Nap Aa-1 BRA80 C 389 (M⁺ + 1) Ca-168 2,3DFPh H H 5-Ind Aa-2 BRA80 C 378 (M⁺ + 1) Ca-169 2,3DFPh H H 1Me-5-1HIdz Aa-5 BRA80 C 393 (M⁺ + 1) Ca-170 2,4DFPh H H 2-Nap Aa-1 BRA81 C 389 (M⁺ + 1) Ca-171 2,4DFPh H H 5-Ind Aa-2 BRA81 C 378 (M⁺ + 1) Ca-172 2,4DFPh H H 1Me-5-Ind Aa-3 BRA81 C 392 (M⁺ + 1) Ca-173 2,4DFPh H H 1Me-5-1HIdz Aa-5 BRA81 C 393 (M⁺ + 1) Ca-174 2,5DFPh H H 2-Nap Aa-1 BRA82 C 389 (M⁺ + 1) Ca-175 2,5DFPh H H 1Me-5-Ind Aa-3 BRA82 C 392 (M⁺ + 1) Ca-176 2,5DFPh H H 1Me-5-1HIdz Aa-5 BRA82 C 393 (M⁺ + 1) Ca-177 2,6DFPh H H 2-Nap Aa-1 BRA83 C 389 (M⁺ + 1) Ca-178 2,6DFPh H H 1Me-5-Ind Aa-3 BRA83 C 392 (M⁺ + 1) Ca-179 2,6DFPh H H 5-1HIdz Aa-4 BRA83 C 379 (M⁺ + 1) Ca-180 2,6DFPh H H 1Me-5-1HIdz Aa-5 BRA83 C 393 (M⁺ + 1) Ca-181 3,4DFPh H H 2-Nap Aa-1 BRA84 C 389 (M⁺ + 1) Ca-182 3,4DFPh H H 5-Ind Aa-2 BRA84 C 378 (M⁺ + 1) Ca-183 3,4DFPh H H 1Me-5-1HIdz Aa-5 BRA84 C 393 (M⁺ + 1) Ca-184 3,5DFPh H H 2-Nap Aa-1 BRA85 C 389 (M⁺ + 1) Ca-185 3,5DFPh H H 1Me-5-Ind Aa-3 BRA85 C 392 (M⁺ + 1) Ca-186 3,5DFPh H H 5-1HIdz Aa-4 BRA85 C 379 (M⁺ + 1) Ca-187 3,5DFPh H H 1Me-5-1HIdz Aa-6 BRA85 C 393 (M⁺ + 1) Ca-188 2,3(CF₃)₂Ph H H 2-Nap Aa-1 BRA63 C 489 (M⁺ + 1) Ca-189 2,3(CF₃)₂Ph H H 1Me-5-Ind Aa-3 BRA63 C 492 (M⁺ + 1) Ca-190 2,3(CF₃)₂Ph H H 1Me-5-1HIdz Aa-5 BRA63 C 493 (M⁺ + 1) Ca-191 2,4(CF₃)₂Ph H H 2-Nap Aa-1 BRA64 C 489 (M⁺ + 1) Ca-192 2,4(CF₃)₂Ph H H 1Me-5-1HIdz Aa-5 BRA64 C 493 (M⁺ + 1) Ca-193 2,5(CF₃)₂Ph H H 2-Nap Aa-1 BRA65 C 489 (M⁺ + 1) Ca-194 2,5(CF₃)₂Ph H H 5-Ind Aa-2 BRA65 C 478 (M⁺ + 1) Ca-195 2,5(CF₃)₂Ph H H 1Me-5-1HIdz Aa-5 BRA65 C 493 (M⁺ + 1) Ca-196 2,5(CF₃)₂Ph H H 3-Qu Aa-7 BRA65 C 490 (M⁺ + 1) Ca-197 3,4(CF₃)₂Ph H H 2-Nap Aa-1 BRA66 C 489 (M⁺ + 1) Ca-198 3,4(CF₃)₂Ph H H 1Me-5-Ind Aa-3 BRA66 C 492 (M⁺ + 1) Ca-199 3,4(CF₃)₂Ph H H 5-1HIdz Aa-4 BRA66 C 479 (M⁺ + 1) Ca-200 3,4(CF₃)₂Ph H H 1Me-5-1HIdz Aa-5 BRA66 C 493 (M⁺ + 1) Ca-201 3,5(CF₃)₂Ph H H 5-Ind Aa-2 BRA17 C 478 (M⁺ + 1) Ca-202 3,5(CF₃)₂Ph H H 5-1HIdz Aa-4 BRA17 C 479 (M⁺ + 1) Ca-203 3,5(CF₃)₂Ph H H 1Me-5-1HIdz Aa-5 BRA17 C 493 (M⁺ + 1) Ca-204 2-Furyl H H 2-Nap Aa-1 BRA35 C 343 (M⁺ + 1) Ca-205 2-Furyl H H 5-Ind Aa-2 BRA35 C 332 (M⁺ + 1) Ca-206 2-Furyl H H 1Me-5-1HIdz Aa-5 BRA35 C 347 (M⁺ + 1) Ca-207 2-Furyl H H 3-Qu Aa-7 BRA35 C 344 (M⁺ + 1) Ca-208 3-Furyl H H 1Me-5-Ind Aa-3 BRA67 C 346 (M⁺ + 1) Ca-209 3-Furyl H H 5-1HIdz Aa-4 BRA67 C 333 (M⁺ + 1) Ca-210 3-Furyl H H 1Me-5-1HIdz Aa-5 BRA67 C 347 (M⁺ + 1) Ca-211 2-Thienyl H H 2-Nap Aa-1 BRA36 C 359 (M⁺ + 1) Ca-212 2-Thienyl H H 1Me-5Ind Aa-3 BRA36 C 362 (M⁺ + 1) Ca-213 2-Thienyl H H 1Me-5-1HIdz Aa-5 BRA36 C 363 (M⁺ + 1) Ca-214 2-Thienyl H H 1Et-5-1HIdz Aa-28 BRA36 C 377 (M⁺ + 1) Ca-215 3-Thienyl H H 5-Ind Aa-2 BRA68 C 348 (M⁺ + 1) Ca-216 3-Thienyl H H 1Me-5-Ind Aa-3 BRA68 C 362 (M⁺ + 1) Ca-217 3-Thienyl H H 5-1HIdz Aa-4 BRA68 C 349 (M⁺ + 1) Ca-218 3-Thienyl H H 1Me-5-1HIdz Aa-5 BRA68 C 363 (M⁺ + 1) Ca-219 3-Thienyl H H 5-Bzt Aa-38 BRA68 C 366 (M⁺ + 1) Ca-220 3-Thienyl H H 3-Qu Aa-7 BRA68 C 360 (M⁺ + 1) Ca-221 3-Thienyl H H 1Et-5-1HIdz Aa-28 BRA68 C 377 (M⁺ + 1) Ca-222 2-Py H H 5-Ind Aa-2 BRA69 C 343 (M⁺ + 1) Ca-223 2-Py H H 1Me-5-1HIdz Aa-5 BRA69 C 358 (M⁺ + 1) Ca-224 2-Py H H 5-Bzt Aa-38 BRA69 C 361 (M⁺ + 1) Ca-225 3-Py H H 2-Nap Aa-1 BRA70 C 354 (M⁺ + 1) Ca-226 3-Py H H 5-Ind Aa-2 BRA70 C 343 (M⁺ + 1) Ca-227 3-Py H H 1Me-5-Ind Aa-3 BRA70 C 357 (M⁺ + 1) Ca-228 3-Py H H 1Me-5-1HIdz Aa-5 BRA70 C 358 (M⁺ + 1) Ca-229 3-Py H H 1Et-5-1HIdz Aa-28 BRA70 C 372 (M⁺ + 1) Ca-230 4-Py H H 2-Nap Aa-1 BRA26 C 354 (M⁺ + 1) Ca-231 4-Py H H 5-Ind Aa-2 BRA26 C 343 (M⁺ + 1) Ca-232 4-Py H H 1Me-5-Ind Aa-3 BRA26 C 357 (M⁺ + 1) Ca-233 4-Py H H 5-1HIdz Aa-4 BRA26 C 344 (M⁺ + 1) Ca-234 4-Py H H 1Me-5-1HIdz Aa-5 BRA26 C 358 (M⁺ + 1) Ca-235 4-Py H H 5-Bzt Aa-38 BRA26 C 361 (M⁺ + 1) Ca-236 4-Py H H 3-Qu Aa-7 BRA26 C 355 (M⁺ + 1) Ca-237 4-Py H H 1Et-5-1HIdz Aa-28 BRA26 C 372 (M⁺ + 1) Ca-238 2DMAPh H H 2-Nap Aa-1 BRA86 C 396 (M⁺ + 1) Ca-239 2DMAPh H H 5-Ind Aa-2 BRA86 C 385 (M⁺ + 1) Ca-240 2DMAPh H H 1Me-5-1HIdz Aa-5 BRA86 C 400 (M⁺ + 1) Ca-241 2DMAPh H H 5-Bzt Aa-38 BRA86 C 403 (M⁺ + 1) Ca-242 2DMAPh H H 1Et-5-1HIdz Aa-28 BRA86 C 414 (M⁺ + 1) Ca-243 3DMAPh H H 1Me-5-Ind Aa-3 BRA87 C 399 (M⁺ + 1) Ca-244 3DMAPh H H 5-1HIdz Aa-4 BRA87 C 386 (M⁺ + 1) Ca-245 3DMAPh H H 1Me-5-1HIdz Aa-5 BRA87 C 400 (M⁺ + 1) Ca-246 3DMAPh H H 5-Bzt Aa-38 BRA87 C 403 (M⁺ + 1) Ca-247 3DMAPh H H 3-Qu Aa-7 BRA87 C 397 (M⁺ + 1) Ca-248 4DMAPh H H 2-Nap Aa-1 BRA21 C 396 (M⁺ + 1) Ca-249 4DMAPh H H 1Me-5-Ind Aa-3 BRA21 C 399 (M⁺ + 1) Ca-250 4DMAPh H H 1Me-5-1HIdz Aa-5 BRA21 C 400 (M⁺ + 1) Ca-251 4DMAPh H H 3-Qu Aa-7 BRA21 C 397 (M⁺ + 1) Ca-252 4DMAPh H H 1Et-5-1HIdz Aa-28 BRA21 C 414 (M⁺ + 1) Ca-253 1-Nap H H 2-Nap Aa-1 BRA16 C 403 (M⁺ + 1) Ca-254 1-Nap H H 5-Ind Aa-2 BRA16 C 392 (M⁺ + 1) Ca-255 1-Nap H H 1Me-5-1HIdz Aa-5 BRA16 C 407 (M⁺ + 1) Ca-256 1-Nap H H 5-Bzt Aa-38 BRA16 C 410 (M⁺ + 1) Ca-257 2-Nap H H 2-Nap Aa-1 BRA1 C 403 (M⁺ + 1) Ca-258 2-Nap H H 1Me-5-Ind Aa-3 BRA1 C 406 (M⁺ + 1) Ca-259 2-Nap H H 5-1HIdz Aa-4 BRA1 C 393 (M⁺ + 1) Ca-260 2-Nap H H 1Me-5-1HIdz Aa-5 BRA1 C 407 (M⁺ + 1) Ca-261 2-Nap H H 5-Bzt Aa-38 BRA1 C 410 (M⁺ + 1) Ca-262 5-Ind H H 2-Nap Aa-1 BRA2 C 392 (M⁺ + 1) Ca-263 5-Ind H H 5-Ind Aa-2 BRA2 C 381 (M⁺ + 1) Ca-264 5-Ind H H 1Me-5-1HIdz Aa-5 BRA2 C 396 (M⁺ + 1) Ca-265 5-Ind H H 3-Qu Aa-7 BRA2 C 393 (M⁺ + 1) Ca-266 5-Ind H H 1Et-5-1HIdz Aa-28 BRA2 C 410 (M⁺ + 1) Ca-267 1Me-5-1HIdz H H 2-Nap Aa-1 BRA6 C 407 (M⁺ + 1) Ca-268 1Me-5-1HIdz H H 1Me-5-Ind Aa-3 BRA6 C 410 (M⁺ + 1) Ca-269 1Me-5-1HIdz H H 1Me-5-1HIdz Aa-5 BRA6 C 411 (M⁺ + 1) Ca-270 1Me-5-1HIdz H H 5-Bzt Aa-38 BRA6 C 414 (M⁺ + 1)

TABLE Cb-1

LCMS Exp. Rx Y Zx AR SM1 SM2 method RTime Mass Cb-1 cPen H H 2-Nap Aa-1 BRA28 C 345 (M⁺ + 1) Cb-2 cPen H H 5-Ind Aa-2 BRA28 C 334 (M⁺ + 1) Cb-3 cPen H H 1Me-5-Ind Aa-3 BRA28 C 348 (M⁺ + 1) Cb-4 cPen H H 5-1HIdz Aa-4 BRA28 C 335 (M⁺ + 1) Cb-5 cPen H H 1Me-5-1HIdz Aa-5 BRA28 C 349 (M⁺ + 1) Cb-6 cPen H H 5-Bzt Aa-38 BRA28 C 352 (M⁺ + 1) Cb-7 cPen H H 3-Qu Aa-7 BRA28 C 346 (M⁺ + 1) Cb-8 cPen H H 1Et-5-1HIdz Aa-28 BRA28 C 363 (M⁺ + 1) Cb-9 nBu H H 2-Nap Aa-1 BRA31 C 333 (M⁺ + 1) Cb-10 nBu H H 5-Ind Aa-2 BRA31 C 322 (M⁺ + 1) Cb-11 nBu H H 1Me-5-1HIdz Aa-5 BRA31 C 337 (M⁺ + 1) Cb-12 iBu H H 2-Nap Aa-1 BRA20 C 333 (M⁺ + 1) Cb-13 iBu H H 1Me-5-Ind Aa-3 BRA20 C 336 (M⁺ + 1) Cb-14 iBu H H 1Me-5-1HIdz Aa-5 BRA20 C 337 (M⁺ + 1) Cb-15 iBu H H 5-Bzt Aa-38 BRA20 C 340 (M⁺ + 1) Cb-16 iBu H H 1Et-5-1HIdz Aa-28 BRA20 C 351 (M⁺ + 1) Cb-17 2-Indan H H 2-Nap Aa-1 BRA42 C 393 (M⁺ + 1) Cb-18 2-Indan H H 5-Ind Aa-2 BRA42 C 382 (M⁺ + 1) Cb-19 2-Indan H H 1Me-5-Ind Aa-3 BRA42 C 396 (M⁺ + 1) Cb-20 2-Indan H H 5-1HIdz Aa-4 BRA42 C 382 (M⁺ + 1) Cb-21 2-Indan H H 1Me-5-1HIdz Aa-5 BRA42 C 397 (M⁺ + 1) Cb-22 2-Indan H H 5-Bzt Aa-38 BRA42 C 400 (M⁺ + 1) Cb-23 2-Indan H H 3-Qu Aa-7 BRA42 C 394 (M⁺ + 1) Cb-24 2-Indan H H 1Et-5-1HIdz Aa-28 BRA42 C 411 (M⁺ + 1) Cb-25 4Me-2-Indan H H 5-Ind Aa-2 BRA43 C 396 (M⁺ + 1) Cb-26 4Me-2-Indan H H 5-1HIdz Aa-4 BRA43 C 397 (M⁺ + 1) Cb-27 4Me-2-Indan H H 1Me-5-1HIdz Aa-5 BRA43 C 411 (M⁺ + 1) Cb-28 4Me-2-Indan H H 3-Qu Aa-7 BRA43 C 408 (M⁺ + 1) Cb-29 5Me-2-Indan H H 2-Nap Aa-1 BRA44 C 407 (M⁺ + 1) Cb-30 5Me-2-Indan H H 5-Ind Aa-2 BRA44 C 396 (M⁺ + 1) Cb-31 5Me-2-Indan H H 5-1HIdz Aa-4 BRA44 C 397 (M⁺ + 1) Cb-32 5Me-2-Indan H H 1Me-5-1HIdz Aa-5 BRA44 C 411 (M⁺ + 1) Cb-33 5Me-2-Indan H H 5-Bzt Aa-38 BRA44 C 414 (M⁺ + 1) Cb-34 5Me-2-Indan H H 1Et-5-1HIdz Aa-28 BRA44 C 425 (M⁺ + 1) Cb-35 4,7DMe-2-Indan H H 5-Ind Aa-2 BRA45 C 410 (M⁺ + 1) Cb-36 4,7DMe-2-Indan H H 5-1HIdz Aa-4 BRA45 C 411 (M⁺ + 1) Cb-37 4,7DMe-2-Indan H H 1Me-5-1HIdz Aa-5 BRA45 C 425 (M⁺ + 1) Cb-38 5,6DMe-2-Indan H H 2-Nap Aa-1 BRA46 C 421 (M⁺ + 1) Cb-39 5,6DMe-2-Indan H H 1Me-5-1HIdz Aa-5 BRA46 C 425 (M⁺ + 1) Cb-40 5F-2-Indan H H 2-Nap Aa-1 BRA47 C 411 (M⁺ + 1) Cb-41 5F-2-Indan H H 5-Ind Aa-2 BRA47 C 400 (M⁺ + 1) Cb-42 5F-2-Indan H H 5-1HIdz Aa-4 BRA47 C 401 (M⁺ + 1) Cb-43 5F-2-Indan H H 1Me-5-1HIdz Aa-5 BRA47 C 415 (M⁺ + 1) Cb-44 5F-2-Indan H H 5-Bzt Aa-38 BRA47 C 418 (M⁺ + 1) Cb-45 5F-2-Indan H H 3-Qu Aa-7 BRA47 C 412 (M⁺ + 1) Cb-46 5F-2-Indan H H 1Et-5-1HIdz Aa-28 BRA47 C 429 (M⁺ + 1) Cb-47 4F-2-Indan H H 2-Nap Aa-1 BRA48 C 411 (M⁺ + 1) Cb-48 4F-2-Indan H H 1Me-5-Ind Aa-3 BRA48 C 414 (M⁺ + 1) Cb-49 4F-2-Indan H H 1Me-5-1HIdz Aa-5 BRA48 C 415 (M⁺ + 1) Cb-50 4,7DF-2-Indan H H 2-Nap Aa-1 BRA49 C 429 (M⁺ + 1) Cb-51 4.7DF-2-Indan H H 1Me-5-Ind Aa-3 BRA49 C 432 (M⁺ + 1) Cb-52 4,7DF-2-Indan H H 1Me-5-1HIdz Aa-5 BRA49 C 433 (M⁺ + 1) Cb-53 5,6DF-2-Indan H H 2-Nap Aa-1 BRA50 C 429 (M⁺ + 1) Cb-54 5,6DF-2-Indan H H 5-Ind Aa-2 BRA50 C 418 (M⁺ + 1) Cb-55 5,6DF-2-Indan H H 1Me-5-Ind Aa-3 BRA50 C 432 (M⁺ + 1) Cb-56 5,6DF-2-Indan H H 5-1HIdz Aa-4 BRA50 C 419 (M⁺ + 1) Cb-57 5,6DF-2-Indan H H 1Me-5-1HIdz Aa-5 BRA50 C 433 (M⁺ + 1) Cb-58 5,6DF-2-Indan H H 5-Bzt Aa-38 BRA50 C 436 (M⁺ + 1) Cb-59 5,6DF-2-Indan H H 3-Qu Aa-7 BRA50 C 430 (M⁺ + 1) Cb-60 5,6DF-2-Indan H H 1Et-5-1HIdz Aa-28 BRA50 C 447 (M⁺ + 1) Cb-61 4Cl-2-Indan H H 5-Ind Aa-2 BRA51 C 416 (M⁺ + 1) Cb-62 4Cl-2-Indan H H 1Me-5-1HIdz Aa-5 BRA51 C 431 (M⁺ + 1) Cb-63 4Cl-2-Indan H H 5-Bzt Aa-38 BRA51 C 434 (M⁺ + 1) Cb-64 5Cl-2-Indan H H 2-Na Aa-1 BRA52 C 427 (M⁺ + 1) Cb-65 5Cl-2-Indan H H 5-Ind Aa-2 BRA52 C 416 (M⁺ + 1) Cb-66 5Cl-2-Indan H H 1Me-5-1HIdz Aa-5 BRA52 C 431 (M⁺ + 1) Cb-67 5Cl-2-Indan H H 3-Qu Aa-7 BRA52 C 428 (M⁺ + 1) Cb-68 5Cl-2-Indan H H 1Et-5-1HIdz Aa-28 BRA52 C 445 (M⁺ + 1) Cb-69 4,7DCl-2-Indan H H 2-Nap Aa-1 BRA53 C 462 (M⁺ + 1) Cb-70 4,7DCl-2-Indan H H 5-Ind Aa-2 BRA53 C 451 (M⁺ + 1) Cb-71 4,7DCl-2-Indan H H 1Me-5-1HIdz Aa-5 BRA53 C 466 (M⁺ + 1) Cb-72 5,6DCl-2-Indan H H 2-Nap Aa-1 BRA54 C 462 (M⁺ + 1) Cb-73 5,6DCl-2-Indan H H 1Me-5-Ind Aa-3 BRA54 C 465 (M⁺ + 1) Cb-74 5,6DCl-2-Indan H H 1Me-5-1HIdz Aa-5 BRA54 C 466 (M⁺ + 1) Cb-75 5,6DCl-2-Indan H H 5-Bzt Aa-38 BRA54 C 469 (M⁺ + 1) Cb-76 5,6DCl-2-Indan H H 3-Qu Aa-7 BRA54 C 483 (M⁺ + 1) Cb-77 5,6DCl-2-Indan H H 1Et-5-1HIdz Aa-28 BRA54 C 480 (M⁺ + 1) Cb-78 4MeO-2-Indan H H 5-Ind Aa-2 BRA55 C 412 (M⁺ + 1) Cb-79 4MeO-2-Indan H H 5-1HIdz Aa-4 BRA55 C 413 (M⁺ + 1) Cb-80 4MeO-2-Indan H H 1Me-5-IHIdz Aa-5 BRA55 C 427 (M⁺ + 1) Cb-81 5MeO-2-Indan H H 2-Nap Aa-1 BRA56 C 423 (M⁺ + 1) Cb-82 5MeO-2-Indan H H 5-Ind Aa-2 BRA56 C 412 (M⁺ + 1) Cb-83 5MeO-2-Indan H H 1Me-5-1HIdz Aa-5 BRA56 C 427 (M⁺ + 1) Cb-84 5MeO-2-Indan H H 5-Bzt Aa-38 BRA56 C 430 (M⁺ + 1) Cb-90 5,6DMeO-2-Indan H H 2-Nap Aa-1 BRA57 C 453 (M⁺ + 1) Cb-91 5,6DMeO-2-Indan H H 1Me-5-Ind Aa-3 BRA57 C 456 (M⁺ + 1) Cb-92 5,6DMeO-2-Indan H H 1Me-5-1HIdz Aa-5 BRA57 C 457 (M⁺ + 1) Cb-93 5,6DMeO-2-Indan H H 5-Bzt Aa-38 BRA57 C 460 (M⁺ + 1) Cb-94 5,6DMeO-2-Indan H H 3-Qu Aa-7 BRA57 C 454 (M⁺ + 1) Cb-95 5,6-DMeO-2-Indan H H 1Et-5-1HIdz Aa-28 BRA57 C 471 (M⁺ + 1) Cb-85 cHex H H 2-Nap Aa-1 BRA58 C 359 (M⁺ + 1) Cb-86 cHex H H 5-Ind Aa-2 BRA58 C 348 (M⁺ + 1) Cb-87 cHex H H 1Me-5-Ind Aa-3 BRA58 C 362 (M⁺ + 1) Cb-88 cHex H H 5-1HIdz Aa-4 BRA58 C 349 (M⁺ + 1) Cb-89 cHex H H 1Me-5-1HIdz Aa-5 BRA58 C 363 (M⁺ + 1)

Reference Examples Intermediate Ab-1 to Ab-47 Synthesis of methyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(naphthalen-2-yl)phenyl]propionate (Intermediate Ab-1)

Compound No. Aa-1 (253.2 mg), bispinacolate diboron (202.6 mg, Ald), PdCl₂(dppf) (43.4 mg) and potassium acetate (289 mg) were added to DMF (5.7 ml), and stirred with heating at 80° C. for 20 hours under argon gas atmosphere. The reaction mixture was added with ethyl acetate (200 ml), washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Ab-1, 194.6 mg).

Typical examples of the compounds of the present invention including those mentioned above that can be obtained by reacting and treating corresponding starting compounds according to the synthesis method of Intermediate Ab-1 are shown in Table-Ab-1.

In the column indicated as “Mass” in the table, data of mass spectra measured by fast atom bombardment mass spectrometry (FAB-MS) are shown.

TABLE Ab-1

Exp. AR Mass Ab-1 2-Nap 417 (M⁺ + 1) Ab-2 5-Ind 406 (M⁺ + 1) Ab-3 1Me-5-Ind 420 (M⁺ + 1) Ab-4 5-1HIdz 407 (M⁺ + 1) Ab-5 1Me-5-1HIdz 421 (M⁺ + 1) Ab-6 5-BF 410 (M⁺ + 1) Ab-7 3-Qu 418 (M⁺ + 1) Ab-8 1-Nap 417 (M⁺ + 1) Ab-9 6MeO-2-Nap 447 (M⁺ + 1) Ab-10 6(Me₂N)-2-Nap 460 (M⁺ + 1) Ab-11 4-Ind 406 (M⁺ + 1) Ab-12 1Me-4-Ind 420 (M⁺ + 1) Ab-13 6-Ind 406 (M⁺ + 1) Ab-14 1Me-6-Ind 420 (M⁺ + 1) Ab-15 2-Ind 406 (M⁺ + 1) Ab-16 1Me-2-Ind 420 (M⁺ + 1) Ab-17 3-Ind 406 (M⁺ + 1) Ab-18 1Me-3-Ind 420 (M⁺ + 1) Ab-19 1iPr-5-Ind 448 (M⁺ + 1) Ab-20 1cPen-5-Ind 474 (M⁺ + 1) Ab-21 3Me-5-Ind 420 (M⁺ + 1) Ab-22 1,3DMe-5-Ind 434 (M⁺ + 1) Ab-23 1,2,3triMe-5-Ind 448 (M⁺ + 1) Ab-24 4-1HIdz 407 (M⁺ + 1) Ab-25 1Me-4-1HIdz 421 (M⁺ + 1) Ab-26 5-1HIdz 407 (M⁺ + 1) Ab-27 1Me-5-1HIdz 421 (M⁺ + 1) Ab-28 1Et-5-1HIdz 435 (M⁺ + 1) Ab-29 1Pr-5-1HIdz 449 (M⁺ + 1) Ab-30 2Me-5-2HIdz 421 (M⁺ + 1) Ab-31 6-1HIdz 407 (M⁺ + 1) Ab-32 1Me-6-1HIdz 421 (M⁺ + 1) Ab-33 3Me-5-1HIdz 421 (M⁺ + 1) Ab-34 1,3DMe-5-1HIdz 435 (M⁺ + 1) Ab-35 5-BT 423 (M⁺ + 1) Ab-36 2,3DMe-5-BF 435 (M⁺ + 1) Ab-37 5-2ABzt 439 (M⁺ + 1) Ab-38 5-Bzt 434 (M⁺ + 1) Ab-39 2Me-5-Bzt 438 (M⁺ + 1) Ab-40 2,2DMe-5-2ABzt 467 (M⁺ + 1) Ab-41 6-2ABzt 439 (M⁺ + 1) Ab-42 6-Bzt 434 (M⁺ + 1) Ab-43 2Me-6-Bzt 438 (M⁺ + 1) Ab-44 6-Qu 418 (M⁺ + 1) Ab-45 6-IQ 418 (M⁺ + 1) Ab-46 2-BF 407 (M⁺ + 1) Ab-47 2-BT 423 (M⁺ + 1)

Example Da-1 Synthesis of methyl 3-[4-(phenylmethyl)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. Da-1)

According to a procedure described in literature (S. Chowdhury et al., Tetrahedron. Lett., 1999, p. 7599), (Ph₃P)₄Pd (14.8 mg) and a solution of benzyl bromide (corresponding to the substance mentioned in the column of SM2 in Table-Da-1 mentioned later) in dimethoxyethane (1.3 ml) were stirred with heating at 50° C. for 10 minutes under argon atmosphere, then added with Compound Ab-1 (52.4 mg, corresponding to the substance mentioned in the column of SM1 in Table-Da-1 mentioned later), and 2 N sodium carbonate (160 μl), and refluxed by heating for 58 hours. The reaction mixture was added with ethyl acetate (60 ml), washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried, and then concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=8:1) to obtain the title compound (Compound No. Da-1, 33.2 mg).

Example Da-2 Synthesis of 3-[4-(phenylmethyl)-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. Da-2)

According to the procedure described in the synthesis method of Compound Ca-2 provided that the reaction was performed for 3 hours, Compound No. Da-1 (28.2 mg) and 2 N aqueous sodium hydroxide (38 μl) were reacted and treated to obtain the title compound (Compound No. Da-2, 23.7 mg).

Examples Da-1 to Da-70

Typical examples of the compounds of the present invention including those mentioned in the examples described above, that can be obtained by reacting and treating corresponding starting compounds according to the methods described in Examples Da-1 and Da-2, are shown in Table-Da-1 and Table-Da-2.

The substances mentioned in the columns of “SM1” in the tables correspond to reaction intermediates, and those mentioned in the columns of “SM2” in the tables correspond to the acid halide mentioned in Example Da-1. The halide reagents mentioned in the columns of “SM2” with the symbols of “HAL (number))” are those mentioned in Table-Ha. The regents for which cells of the columns of “Manufacturer” are blank in the tables are synthesized according to a method described in ordinary chemical literature.

TABLE Ha Reagent Name of reagent Manufacturer HAL-1 Benzyl bromide Ald HAL-2 4-Methoxybenzyl bromide Ald HAL-3 3-Methoxybenzyl bromide Ald HAL-4 2-Methoxybenzyl bromide Ald HAL-5 4-Methylbenzyl bromide Ald HAL-6 3-Methylbenzyl bromide Ald HAL-7 2-Methylbenzyl bromide Ald HAL-8 4-Trifluoromethylbenzyl bromide Ald HAL-9 3-Trifluoromethylbenzyl bromide Ald HAL-10 2-Trifluoromethylbenzyl bromide Ald HAL-11 4-Chlorobenzyl bromide Ald HAL-12 3-Chlorobenzyl bromide Ald HAL-13 2-Chlorobenzyl bromide Ald HAL-14 4-Fluorobenzyl bromide Ald HAL-15 3-Fluorobenzyl bromide Ald HAL-16 2-Fluorobenzyl bromide Ald HAL-17 1-Bromo-2-phenyl ethane Ald HAL-18 1-Bromo-2-(4-chloro phenyl) ethane Ald HAL-19 1-Bromo-2-(3-chloro phenyl) ethane HAL-20 1-Bromo-2-(2-chloro phenyl) ethane HAL-21 1-Bromo-2-(4-dimethyl aminophenyl) ethane HAL-22 Benzoyl chloride TCI HAL-23 Acetyl chloride WAKO HAL-24 i-Butyryl chloride Ald HAL-25 Cyclohexylcarbonyl chloride Ald HAL-26 4-Methoxybenzoyl chloride TCI HAL-27 4-Methylbenzoyl chloride Ald HAL-28 4-Chlorobenzoyl chloride TCI HAL-29 Phenylacetyl chloride WAKO HAL-30 2-Phenylpropionyl chloride TCI

TABLE Da-1

LCMS Exp. Rx Y Zx AR SM1 SM2 method RTime Mass Da-1 Ph Me H 2-Nap Ab-1 HAL-1 D N.D Da-2 Ph H H 2-Nap Da-1 — C 367 (M⁺ + 1) Da-3 Ph Me H 5-Ind Ab-2 HAL-1 Da-4 Ph H H 5-Ind Da-3 — Da-5 Ph Me H 1Me-5-Ind Ab-3 Ha-1 C 384 (M⁺ + 1) Da-6 Ph H H 1Me-5-Ind Da-5 — C 369 (M⁺ + 1) Da-7 Ph Me H 5-1HIdz Ab-4 Ha-1 Da-8 Ph H H 5-1HIdz Da-7 — Da-9 Ph Me H 1Me-5-1HIdz Ab-5 HAL-1 C 385 (M⁺ + 1) Da-10 Ph H H 1Me-5-1HIdz Da-9 — C 370 (M⁺ + 1) Da-11 4MeOPh H H 2-Nap Ab-1 HAL-2 Da-12 4MeOPh H H 5-Ind Ab-2 HAL-2 Da-13 4MeOPh H H 1Me-5-1HIdz Ab-5 HAL-2 Da-14 3MeOPh H H 2-Nap Ab-1 HAL-3 C 397 (M⁺ + 1) Da-15 3MeOPh H H 5-Ind Ab-2 HAL-3 Da-16 3MeOPh H H 1Me-5-1HIdz Ab-5 HAL-3 Da-17 2MeOPh H H 2-Na Ab-1 HAL-4 Da-18 2MeOPh H H 5-Ind Ab-2 HAL-4 Da-19 2MeOPh H H 1Me-5-1HIdz Ab-5 HAL-4 Da-20 4MePh H H 2-Nap Ab-1 HAL-5 C 381 (M⁺ + 1) Da-21 4MePh H H 5-Ind Ab-2 HAL-5 Da-22 4MePh H H 1Me-5-1HIdz Ab-5 HAL-5 Da-23 3MePh H H 2-Nap Ab-1 HAL-6 Da-24 3MePh H H 5-Ind Ab-2 HAL-6 Da-25 3MePh H H 1Me-5-1HIdz Ab-5 HAL-6 Da-26 2MePh H H 2-Nap Ab-1 HAl-7 C 381 (M⁺ + 1) Da-27 2MePh H H 5-Ind Ab-2 HAl-7 C 370 (M⁺ + 1) Da-28 2MePh H H 1Me-5-1HIdz Ab-5 HAl-7 Da-29 4CF₃Ph H H 2-Nap Ab-1 HAL-8 Da-30 4CF₃Ph H H 5-Ind Ab-2 HAL-8 Da-31 4CF₃Ph H H 1Me-5-1HIdz Ab-5 HAL-8 Da-32 3CF₃Ph H H 2-Nap Ab-1 HAL-9 Da-33 3CF₃Ph H H 5-Ind Ab-2 HAL-9 Da-34 3CF₃Ph H H 1Me-5-1HIdz Ab-5 HAL-9 Da-35 2CF₃Ph H H 2-Nap Ab-1 HAL-10 Da-36 2CF₃Ph H H 5-Ind Ab-2 HAL-10 Da-37 2CF₃Ph H H 1Me-5-1HIdz Ab-5 HAL-10 Da-38 4ClPh H H 2-Nap Ab-1 HAL-11 C 401 (M⁺ + 1) Da-39 4ClPh H H 5-Ind Ab-2 HAL-11 C 390 (M⁺ + 1) Da-40 4ClPh H H 1Me-5-1HIdz Ab-5 HAL-11 Da-41 3ClPh H H 2-Nap Ab-1 HAL-12 Da-42 3ClPh H H 5-Ind Ab-2 HAL-12 Da-43 3ClPh H H 1Me-5-1HIdz Ab-5 HAL-12 Da-44 2ClPh H H 2-Nap Ab-1 HAL-13 Da-45 2ClPh H H 5-Ind Ab-2 HAL-13 Da-46 2ClPh H H 1Me-5-1HIdz Ab-5 HAL-13 Da-47 4FPh H H 2-Nap Ab-1 HAL-14 C 385 (M⁺ + 1) Da-48 4FPh H H 5-Ind Ab-2 HAL-14 Da-49 4FPh H H 1Me-5-1HIdz Ab-5 HAL-14 C 389 (M⁺ + 1) Da-50 3FPh H H 2-Nap Ab-1 HAL-15 Da-51 3FPh H H 5-Ind Ab-2 HAL-15 Da-52 3FPh H H 1Me-5-1HIdz Ab-5 HAL-15 Da-53 2FPh H H 2-Nap Ab-1 HAL-16 Da-54 2FPh H H 5-Ind Ab-2 HAL-16 Da-55 2FPh H H 1Me-5-1HIdz Ab-5 HAL-16 Da-56 Bn H H 2-Nap Ab-1 HAL-17 C 381 (M⁺ + 1) Da-57 Bn H H 5-Ind Ab-2 HAL-17 Da-58 Bn H H 1Me-5-1HIdz Ab-5 HAL-17 C 419 (M⁺ + 1) Da-59 4ClBn H H 2-Nap Ab-1 HAL-18 Da-60 4ClBn H H 5-Ind Ab-2 HAL-18 Da-61 4ClBn H H 1Me-5-1HIdz Ab-5 HAL-18 C 385 (M⁺ + 1) Da-62 3ClBn H H 2-Nap Ab-1 HAL-19 C 415 (M⁺ + 1) Da-63 3ClBn H H 5-Ind Ab-2 HAL-19 Da-64 3ClBn H H 1Me-5-1HIdz Ab-5 HAL-19 Da-65 2ClBn H H 2-Nap Ab-1 HAL-20 Da-66 2ClBn H H 5-Ind Ab-2 HAL-20 Da-67 2ClBn H H 1Me-5-1HIdz Ab-5 HAL-20 Da-68 4DMABn H H 2-Nap Ab-1 HAL-21 C 424 (M⁺ + 1) Da-69 4DMABn H H 5-Ind Ab-2 HAL-21 C 413 (M⁺ + 1) Da-70 4DMABn H H 1Me-5-1HIdz Ab-5 HAL-21

Example Ea-1 Synthesis of methyl 3-[4-(phenylcarbonyl)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. Ea-1)

According to a procedure described in literature (Y. Urawa et al, Tetrahedron. Lett., 2003, p. 271), Compound Ab-1 (112.1 mg, corresponding to the substance mentioned in the column of SM1 in Table-Ea-1 mentioned later), dichlorobis(triphenylphosphine)palladium (18.9 mg, KANTO), and a solution of potassium phosphate (147.1 mg) in toluene (2.6 ml) were added with benzoyl chloride (47 μg, corresponding to the substance mentioned in the column of SM2 in Table-Ea-1), and stirred with heating at 110° C. for 48 hours under nitrogen atmosphere. The reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate, water and saturated brine, dried, and then concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate 7:1) to obtain the title compound (Compound No. Ea-1, 88.3 mg).

Example Ea-2 Synthesis of 3-[4-phenylcarbonyl-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. Ea-2)

According to the procedure described in the synthesis method of Compound Ca-2 with the modification that the reaction was carried out for 3 hour, Compound No. Ea-1 (82.6 mg) and 2 N aqueous sodium hydroxide (105 ml) were reacted and treated to obtain the title compound (Compound No. Ea-2, 70.7 mg).

Examples Ea-1 to Ea-34

Typical examples of the compounds of the present invention including those mentioned in the examples described above, that can be obtained by reacting and treating corresponding starting compounds according to the methods described in Examples Ea-1 and Ea-2, are shown in Table-Ea-1.

The substances mentioned in the column of “SM1” in the table correspond to reaction intermediates, and those mentioned in the column of “SM2” in the table correspond to acid chlorides mentioned in Table Ea-1. The acid chlorides mentioned with the symbols of “HAL (number)” in the column of “SM2” are those mentioned in Table-Ha.

TABLE Ea-1

LCMS Exp. Rx Y Zx AR SM1 SM2 method RTime Mass Ea-1 Ph Me H 2-Nap Ab-1 HAL-22 C 395 (M⁺ + 1) Ea-2 Ph H H 2-Nap Ea-1 — C 381 (M⁺ + 1) Ea-3 Ph Me H 5-Ind Ab-2 HAL-22 Ea-4 Ph H H 5-Ind Ea-3 — Ea-5 Ph Me H 1Me-5-Ind Ab-3 HAL-22 C 398 (M⁺ + 1) Ea-6 Ph H H 1Me-5-Ind Ea-5 — C 384 (M⁺ + 1) Ea-7 Ph Me H 5-1HIdz Ab-4 HAL-22 Ea-8 Ph H H 5-1HIdz Ea-7 — Ea-9 Ph Me H 1Me-5-1HIdz Ab-5 HAL-22 C 399 (M⁺ + 1) Ea-10 Ph H H 1Me-5-1HIdz Ea-9 — C 385 (M⁺ + 1) Ea-11 Me H H 2-Nap Ab-1 HAL-23 C 319 (M⁺ + 1) Ea-12 Me H H 5-Ind Ab-2 HAL-23 C 308 (M⁺ + 1) Ea-13 Me H H 1Me-5-1HIdz Ab-5 HAL-23 Ea-14 iBu H H 2-Nap Ab-1 HAL-24 C 361 (M⁺ + 1) Ea-15 iBu H H 5-Ind Ab-2 HAL-24 Ea-16 iBu H H 1Me-5-1HIdz Ab-5 HAL-24 C 365 (M⁺ + 1) Ea-17 cHex H H 2-Nap Ab-1 HAL-25 C 386 (M⁺ + 1) Ea-18 cHex H H 5-Ind Ab-2 HAL-25 Ea-19 cHex H H 1Me-5-1HIdz Ab-5 HAL-25 Ea-20 4MeOPh H H 2-Nap Ab-1 HAL-26 C 411 (M⁺ + 1) Ea-21 4MeOPh H H 5-Ind Ab-2 HAL-26 C 400 (M⁺ + 1) Ea-22 4MeOPh H H 1Me-5-1HIdz Ab-5 HAL-26 Ea-23 4MePh H H 2-Nap Ab-1 HAL-27 Ea-24 4MePh H H 5-Ind Ab-2 HAL-27 Ea-25 4MePh H H 1Me-5-1HIdz Ab-5 HAL-27 Ea-26 4ClPh H H 2-Nap Ab-1 HAL-28 C 415 (M⁺ + 1) Ea-27 4ClPh H H 5-Ind Ab-2 HAL-28 Ea-28 4ClPh H H 1Me-5-1HIdz Ab-5 HAL-28 Ea-29 Bn H H 2-Nap Ab-1 HAL-29 C 395 (M⁺ + 1) Ea-30 Bn H H 5-Ind Ab-2 HAL-29 Ea-31 Bn H H 1Me-5-1HIdz Ab-5 HAL-29 C 399 (M⁺ + 1) Ea-32 1PhEt H H 2-Nap Ab-1 HAL-30 C 409 (M⁺ + 1) Ea-33 1PhEt H H 5-Ind Ab-2 HAL-30 C 398 (M⁺ + 1) Ea-34 1PhEt H H 1Me-5-1HIdz Ab-5 HAL-30

Reference Examples Intermediate Ac-1 and Ac-2 Synthesis of t-butyldimethylsilyl 3-[3-bromo-4-(t-butyldimethylsilyloxy)phenyl]acrylate (Intermediate Ac-1)

According to the procedure described in the synthesis method of Intermediate 43, 3-[3-bromo-4-hydroxylphenyl]acrylic acid (12.01 g) obtainable from 4-hydroxybenzaldehyde (TCI) by a method known from literature (Y. Nagao et al., Tetrahedron Lett., 1980, p. 4931) was reacted with imidazole (16.01 g) and t-butyldimethylsilyl chloride (7.43 g) and treated to obtain the title compound (Intermediate Ac-1, 17.43 g).

Synthesis of 3-[3-bromo-4-(t-butyldimethylsilyloxy)phenyl]acrylic acid (Intermediate Ac-2)

A solution of Compound Ac-1 (17.43 g) in methanol (100 ml) was added with 1 N hydrochloric acid (5 ml), and stirred at room temperature for 3 hours. The reaction solution was extracted with ethyl acetate (500 ml), and washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. Ac-2, 14.60 g).

Example Ga-1 Synthesis of methyl 3-[3-(1H-indol-5-yl)-4-(3-pyridinemethyloxy)phenyl]acrylate (Compound No. Ga-1) (Step 1)

A solution of Compound Ac-2 (3.06 g), diisopropyl carbodiimide (henceforth abbreviated as “DIC”, 1.33 ml) and dimethylaminopyridine (86.8 mg) in DMF (100 ml) was added with SynPhase-PS-D-series Lantern, Hydroxymethylphenoxy Linker (henceforth abbreviated as “PSL”, 0.035 mmol per lantern, 81 lanterns, Mimotopes), and left standing at room temperature for 16 hours. After the reaction mixture was removed, PSL was washed successively with DMF (100 ml), methanol (100 ml), dichloromethane (100 ml), and THF (100 ml) three times for each, and dried under reduced pressure.

PSL (81 lanterns mentioned above) was added to a solution of tetrabutylammonium fluoride (8.5 ml, Ald, 1 N THF solution) in THF (80 ml), and left standing at room temperature for 23 hours. After the reaction mixture was removed, PSL was successively washed with DMF (100 ml) three times, alternately with DMF:water:acetic acid (75:25:1, 100 ml) and methanol:water:acetic acid (75:25:1, 100 ml) twice for each, alternately with DMF:water (4:1, 100 ml) and methanol:water (4:1, 100 ml) twice for each, and with THF (100 ml), chloroform (100 ml), DMF (100 ml), and chloroform (100 ml) twice for each, and then dried under reduced pressure to obtain PLS-1 (81 lanterns).

(Step 2)

SL-1 (3 lanterns out of those mentioned above) was added to a mixed solution of 3-pyridinemethanol (147.6 μl, corresponding to the substance mentioned in the column of SM1 in Table-Ga-1 mentioned later), DBAB (242.1 mg, Sigma) and Ph₃P (275.6 mg, KANTO) in dehydrated THF (3.24 ml), and left standing at room temperature for 15 hours. After the reaction mixture was removed, PSL was successively washed with THF (3.5 ml) and DMF (3.5 ml) four times for each, alternately with methanol (3.5 ml) and DMF (3.5 ml) twice for each, alternately with DMF (3.5 ml) and dichloromethane (3.5 ml) twice for each, with dichloromethane (3.5 ml) twice, and dried under reduced pressure to obtain PSL-2 (3 vials).

(Step 3)

SL-2 (1 lantern out of those mentioned above) was added to a mixed solution of 1H-indole-5-boronic acid (11.3 mg, corresponding to the substance mentioned in the column of SM2 in Table-Ga-1 mentioned later), (Ph₃P)₄Pd (8.1 mg), and 2 N aqueous cesium carbonate (176 μl) in DMF (800 μl), and heated at 80° C. for 18 hours under argon atmosphere. After the reaction mixture was removed, PSL was successively washed with DMF (1.0 ml) four times, with methanol (1.0 ml) twice, alternately with DMF (1.0 ml) and methanol (1.0 ml) twice for each, alternately with DMF (1.0 ml) and dichloromethane (1.0 ml) twice for each, and with dichloromethane (1.0 ml) twice, and dried under reduced pressure. This PSL was added to a solution of sodium methoxide (175 μl, WAKO, 1 N solution in methanol) in THF:methanol (2:1, 1.5 ml), and left standing at room temperature for 19 hours. After the reaction, PSL was removed, and the reaction solution was added with water (500 μl), and stirred with heating at 60° C. for 3 hours. The reaction solution was concentrated under reduced pressure, then added with water (200 μl) and chloroform (1 ml), and passed through a diatomaceous earth column, and the obtained filtrate was concentrated under reduced pressure to obtain the title compound (Compound No. Ga-1, 10.6 mg).

Examples Ga-1 to Ga-55

Typical examples of the compounds of the present invention including those mentioned in the examples described above, that can be obtained by reacting and treating corresponding starting compounds according to the method described in Example Ga-1, are shown in Table-Ga-1 and Table-Ga-2.

The substances mentioned in the columns of “SM1” in the tables correspond to the alcohol reagent mentioned in Example Ga-1, and those mentioned in the columns of “SM2” in the tables correspond to the boronic acid reagent mentioned in Table Ga-1. The alcohol reagents mentioned in the columns of “SM1” with the symbols of “ALC (number))” are those mentioned in Table-I. The boronic acid reagents mentioned with the symbols of “BRA (number))” in the columns of “SM2” are those mentioned in Table-Ba-1 and Table-Ba-2.

TABLE I Reagent Name of reagent Manufacture ALC-1 Cyclopentanol KANTO ALC-2 Cyclohexanol Ald ALC-3 Benzyl Alcohol Ald ALC-4 2-Methyl-1-propyl alcohol TCI ALC-5 4-Fluorophenetyl alcohol Ald ALC-6 1-Phenylethanol WAKO ALC-7 2-(N-Methylanilino) ethanol TCI ALC-8 2-Hydroxy indane TCI ALC-9 2-Hydroxymethyl-1,4-benzodioxane TCI ALC-10 2-(4-Dimethyl) phenyl ethanol Ald ALC-11 3-Pyridine methanol TCI ALC-12 m-Chlorobenzyl alcohol TCI ALC-13 4-n-Butoxybenzyl alcohol TCI ALC-14 2-Hydroxyacetophenone TCI ALC-15 2-Phenoxy ethanol TCI ALC-16 2-Phenylthio ethanol TCI ALC-17 5-(2-Hydroxyethyl)-4-methylthiazol TCI ALC-18 1-Butanol TCI ALC-19 2-Hydroxyethyl acetate TCI ALC-20 N-(2-Hydroxyethyl) morpholine TCI ALC-21 2-(2-Dimethylaminoethoxy) TCI ALC-22 Methyl glycolate TCI ALC-23 1-Phenyl ethanol TCI ALC-24 2-Chlorobenzyl alcohol TCI ALC-25 3-Chlorobenzyl alcohol TCI ALC-26 4-Chlorobenzyl alcohol TCI ALC-27 2-Methoxybenzyl alcohol TCI ALC-28 3-Methoxybenzyl alcohol TCI ALC-29 4-Methoxybenzyl alcohol TCI

TABLE Ga

LCMS Exp. RxO Y Zx AR SM1 SM2 method RTime Mass Ga-1 3PyMeO H H 5-Ind ALC-11 BRA2 A 3.27 371 (M⁺ + 1) Ga-2 2(PhS)EtO H H 5-Ind ALC-16 BRA2 Ga-3

H H 5-Ind ALC-17 BRA2 A 3.07 405 (M⁺ + 1) Ga-4 nBuO H H 5-Ind ALC-18 BRA2 Ga-5

H H 5-Ind ALC-21 BRA2 Ga-6 cPenO H H 5-Ind ALC-1 BRA2 Ga-7 cHexO H H 5-Ind ALC-2 BRA2 Ga-8 PhMeO H H 5-Ind ALC-3 BRA2 A 3.79 356 (M⁺ + 1) Ga-9 cPenO H H 2-BF ALC-1 BRA18 Ga-10 cHexO H H 2-BF ALC-2 BRA18 Ga-11 2-IndanO H H 2-BF ALC-8 BRA18 A 3.85 397 (M⁺ + 1) Ga-12 3PyMeO H H 2-BF ALC-11 BRA18 Ga-13 2(PhS)EtO H H 2-BF ALC-16 BRA18 A 3.61 417 (M⁺ + 1) Ga-14

H H 2-BF ALC-17 BRA18 Ga-15 nBuO H H 2-BF ALC-18 BRA18 Ga-16

H H 2-BF ALC-21 BRA18 Ga-17 cPenO H H 1Me-5-1HIdz ALC-1 BRA6 Ga-18 cHexO H H 1Me-5-1HIdz ALC-2 BRA6 A 3.74 377 (M⁺ + 1) Ga-19 2-IndanO H H 1Me-5-1HIdz ALC-8 BRA6 Ga-20 3PyMeO H H 1Me-5-1HIdz ALC-11 BRA6 Ga-21 2(PhS)EtO H H 1Me-5-1HIdz ALC-16 BRA6 Ga-22

H H 1Me-5-1HIdz ALC-17 BRA6 Ga-23 nBuO H H 1Me-5-1HIdz ALC-18 BRA6 Ga-24

H H 1Me-5-1HIdz ALC-21 BRA6 Ga-25 3PyMeO H H 1-Nap ALC-11 BRA16 Ga-26 2(PhS)EtO H H 1-Nap ALC-16 BRA16 C 427 (M⁺ + 1) Ga-27

H H 1-Nap ALC-17 BRA16 Ga-28 nBuO H H 1-Nap ALC-18 BRA16 Ga-29

H H 1-Nap ALC-21 BRA16 Ga-30 iPhEtO H H 5-Ind ALC-6 BRA2 Ga-31 iPhEtO H H 2-BF ALC-6 BRA18 Ga-32 iPhEtO H H 1Me-5-1HIdz ALC-6 BRA6 A 3.55 399 (M⁺ + 1) Ga-33 iPhEtO H H 1-Nap ALC-6 BRA16 Ga-34 iPhEtO H H 2-Nap ALC-6 BRA1 Ga-35 iPhEtO H H 2-Nap ALC-6 BRA1 C 395 (M⁺ + 1) Ga-36 iPhEtO H H 5-Ind ALC-6 BRA2 Ga-37 2ClPhMeO H H 2-Nap ALC-24 BRA1 Ga-38 2ClPhMeO H H 5-Ind ALC-24 BRA2 Ga-39 3ClPhMeO H H 2-Nap ALC-25 BRA1 C 415 (M⁺ + 1) Ga-40 3ClPhMeO H H 5-Ind ALC-25 BRA2 Ga-41 4ClPhMeO H H 2-Nap ALC-26 BRA1 Ga-42 4ClPhMeO H H 5-Ind ALC-26 BRA2 C 404 (M⁺ + 1) Ga-43 2MeOPhMeO H H 2-Nap ALC-27 BRA1 Ga-44 2MeOPhMeO H H 5-Ind ALC-27 BRA2 Ga-45 3MeOPhMeO H H 2-Nap ALC-28 BRA1 Ga-46 3MeOPhMeO H H 5-Ind ALC-28 BRA2 Ga-47 4MeOPhMeO H H 2-Nap ALC-29 BRA1 Ga-48 4MeOPhMeO H H 5-Ind ALC-29 BRA2 Ga-49 nBuO H H 3-Qu ALC-18 BRA10 C 348 (M⁺ + 1) Ga-50 nBuO H H 3-Thienyl ALC-18 BRA36 Ga-51 nBuO H H 4-Py ALC-18 BRA26 Ga-52 nBuO H H cPen ALC-18 BRA28 Ga-53 nBuO H H 2FPh ALC-18 BRA32 C 315 (M⁺ + 1) Ga-54 nBuO H H 3FPh ALC-18 BRA33 Ga-55 nBuO H H 4FPh ALC-18 BRA34

Reference Examples Intermediate s-1 to s-52 Synthesis of methyl 3-[4-(4-methylphenylthio)-3-nitrophenyl]acrylate (Intermediate s-1) (Synthesis method SF)

A solution of 3-[4-(4-methylphenylthio)-3-nitrophenyl]acrylic acid (631 mg, MAYB) in a mixture of methanol (12.6 ml), ethyl acetate (6.3 ml) and THF (6.3 ml) was added dropwise to methanol (12.6 ml) beforehand under ice cooling, and then the mixture was added with a solution of thionyl chloride (735 μl, KANTO) in methanol (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 15.5 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (50 ml) for neutralization, and extracted with ethyl acetate (50 ml), and the organic layer was washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate s-1, 659 mg).

Synthesis of methyl 3-[4-(4-methylphenylthio)-3-nitrophenyl]propionate (Intermediate s-2) (Synthesis method SDI)

A solution of Intermediate s-1 (494 mg) in ethyl acetate (75 ml) was added with 10% palladium hydroxide/carbon (150 mg, NE CHEMCAT), and stirred at room temperature for 14 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (75 ml) again, added with 5 N hydrochloric acid (600 μl) and 10% palladium hydroxide/carbon (151 mg), and stirred at room temperature for 22 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate s-2, 419 mg).

Synthesis of methyl 3-[3-bromo-4-(4-methylphenylthio)phenyl]propionate (Intermediate s-3) (Synthesis method SE1)

A solution of hydrobromic acid (690 μl) in methanol (3.2 ml) was added with a solution of Intermediate s-2 (362 mg) in methanol (3.2 ml) under ice cooling. This mixture was added dropwise with an aqueous solution (320 μl) of sodium nitrite (84 mg, WAKO).

An aqueous solution (3.2 ml) of copper(II) bromide (270 mg, WAKO) was heated to 40° C. added dropwise with the previously obtained solution over 20 minutes, and stirred at the same temperature for 1.5 hours.

The reaction mixture was extracted with ethyl acetate (40 ml). The organic layer was washed successively with water and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (Intermediate s-3, 167 mg).

Synthesis of methyl 3-(3-bromo-4-fluorophenyl)acrylate (Intermediate s-4) (Synthesis method SF)

According to the procedure described in the synthesis method of Intermediate n−1 (Synthesis method SF) provided that the reaction was performed for 1 hour, 3-bromo-4-fluorocinnamic acid (3.30 g, LANC) and thionyl chloride (1.5 ml, WAKO) were reacted and treated to obtain the title compound (Intermediate n-25, 3.47 g).

Synthesis of methyl 3-[3-bromo-4-(4-methoxyphenylthio)phenyl]acrylate (Intermediate s-5) (Synthesis method SC)

A solution of Intermediate s-4 (259.1 mg) in DMSO (4 ml) was added with potassium carbonate (156.9 mg) and p-methoxythiophenol (148 μl, TCI), and stirred at 70° C. for 16 hours. The reaction mixture was extracted with ethyl acetate (30 ml), and then the organic layer was washed successively with water and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=8:1) to obtain the title compound (Intermediate s-5, 283.3 mg).

Synthesis of methyl 3-[3-bromo-4-(4-methoxyphenylthio)phenyl)propionate (Intermediate s-6) (Synthesis method SD2)

According to a procedure described in literature [D. J. Hart et al., Journal of Organic Chemistry (J. Org. Chem.), 1987, vol. 52, p. 4665], a solution of Intermediate s-5 (579.1 mg) in dimethoxyethane (40 ml) was added with p-toluenesulfonhydrazide (1.99 g, TCI), and refluxed by heating at 110° C. Then, the reaction mixture was added dropwise with an aqueous solution (40 ml) of sodium acetate (1.54 g, WAKO) over 1 hour, and further stirred for 3 hours. The reaction mixture was extracted with dichloromethane (150 ml), and the organic layer was washed with water, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=7:1) to obtain the title compound (Intermediate s-6, 583.5 mg).

Synthesis of 3-bromo-4-(cyclopentylthio)benzaldehyde (Intermediate s-23) (Synthesis method SC)

A solution of 3-bromo-4-fluorobenzaldehyde (517.4 mg) in DMSO (8 ml) was added with potassium carbonate (514.9 mg) and cyclopentanethiol (250 μl, TCI), and stirred at 90° C. for 17 hours. The reaction mixture was extracted with ethyl acetate (50 ml), and the organic layer was washed successively with water and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=8:1) to obtain the title compound (Intermediate S-23, 644.7 mg).

Synthesis of ethyl 3-[3-bromo-4-(cyclopentylthio)phenyl]acrylate (Intermediate s-24) (Synthesis method SE2)

A solution of Intermediate s-23 (243.7 mg) in 1,2-dimethoxyethane (8 ml) was added with ethyl diethylphosphonoacetate (300 μl, TCI), and added with 60% sodium hydride (49.8 mg) under ice cooling. The reaction mixture was stirred for 10 minutes, then warmed to room temperature, and stirred for 1 hour. The reaction mixture was added with water (5 ml) for quenching, added with dichloromethane (30 ml) for extraction, and washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate s-24, 286.2 mg).

Typical examples of the intermediates including those mentioned above that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-Int. S-1 and Table-Int. S-2. In the tables, intermediate numbers are mentioned in the columns indicated as “Exp”. In the tables, used methods among those described above are mentioned in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”. Further, the compounds indicated as “Single” in the columns of “Single or Double” in Table-Int.S-1 are compounds in which two of the carbon atoms binding the benzene ring and carbonyl group in the compounds are bound with a single bond, and those indicated as “Double” in the same are compounds in which two of the carbon atoms binding the benzene ring and carbonyl group in the compounds are bound with a double bond.

TABLE Int.S

Single or LCMS Exp. Syn. SM1 SM2 Rx—S Y Double method RTime Mass Int.s-5 SC Int.s-4 4MeOPhSH 4MeOPhS Me Double D 5.87 378 (M⁺ + 1) Int.s-6 SD2 Int.s-5 4MeOPhS Me Single C 380 (M⁺ + 1) Int.s-7 SC Int.s-4 2MeOPhSH 2MeOPhS Me Double C 378 (M⁺ + 1) Int.s-8 SD2 Int.s-7 2MeOPhS Me Single C 380 (M⁺ + 1) Int.s-9 SC Int.s-4 3MeOPhSH 3MeOPhS Me Double C 378 (M⁺ + 1) Int.s-10 SD2 Int.s-9 3MeOPhS Me Single C 380 (M⁺ + 1) Int.s-11 SC Int.s-4 2MePhSH 2MePhS Me Double C 368 (M⁺ + 1) Int.s-12 SD2 Int.s-11 2MePhS Me Single D 5.70 N.D Int.s-13 SC Int.s-4 3MePhSH 3MePhS Me Double C 368 (M⁺ + 1) Int.s-14 SD2 Int.s-13 3MePhS Me Single C 366 (M⁺ + 1) Int.s-15 SC Int.s-4 4MePhSH 4MePhS Me Double C 368 (M⁺ + 1) Int.s-16 SD2 Int.s-15 4MePhS Me Single C 366 (M⁺ + 1) Int.s-17 SC Int.s-4 2FPhSH 2FPhS Me Double C 368 (M⁺ + 1) Int.s-18 SD2 Int.s-17 2FPhS Me Single C 370 (M⁺ + 1) Int.s-19 SC Int.s-4 3FPhSH 3FPhS Me Double C 368 (M⁺ + 1) Int.s-20 SD2 Int.s-19 3FPhS Me Single C 370 (M⁺ + 1) Int.s-21 SC Int.s-4 4FPhSH 4FPhS Me Double C 368 (M⁺ + 1) Int.s-22 SD2 Int.s-21 4FPhS Me Single C 370 (M⁺ + 1) Int.s-24 SE2 Int.s-23 cPenS Me Double D 6.35 340 (M⁺ + 1) Int.s-25 SD2 Int.s-24 cPenS Me Single C 342 (M⁺ + 1) Int.s-27 SE2 Int.s-26 cHexS Et Double C 354 (M⁺ + 1) Int.s-28 SD2 Int.s-27 cHexS Et Single C 356 (M⁺ + 1) Int.s-30 SE2 Int.s-29 nPrS Et Double C 328 (M⁺ + 1) Int.s-31 SD2 Int.s-30 nPrS Et Single C 330 (M⁺ + 1) Int.s-33 SE2 Int.s-32 iPrS Et Double C 328 (M⁺ + 1) Int.s-34 SD2 Int.s-33 iPrS Et Single C 330 (M⁺ + 1) Int.s-36 SE2 Int.s-35 nBuS Et Double C 328 (M⁺ + 1) Int.s-37 SD2 Int.s-36 nBuS Et Single C 330 (M⁺ + 1) Int.s-39 SE2 Int.s-38 iBuS Me Double D 5.86 330 (M⁺ + 1) Int.s-40 SD2 Int.s-39 iBuS Me Single D 6.23 330 (M⁺ + 1) Int.s-42 SE2 Int.s-41 2PhEtS Me Double D 6.18 376 (M⁺) Int.s-43 SD2 Int.s-42 2PhEtS Me Single D 6.21 378 (M⁺) Int.s-45 SE2 Int.s-44 4MeOBnS Et Double C 393 (M⁺ + 1) Int.s-46 SD2 Int.s-45 4MeOBnS Et Single C 395 (M⁺ + 1) Int.s-48 SE2 Int.s-47 4FBnS Et Double C 381 (M⁺ + 1) Int.s-49 SD2 Int.s-48 4FBnS Et Single C 383 (M⁺ + 1) Int.s-51 SE2 Int.s-50 2MeBnS Et Double C 377 (M⁺ + 1) Int.s-52 SD2 Int.s-51 2MeBnS Et Single C 379 (M⁺ + 1)

LCMS Exp. Syn. SM1 SM2 Rx—S method RTime Mass Int.s-23 SC cPenSH cPenS C 286 (M⁺ + 1) Int.s-26 SC cHexSH cHexS C 300 (M⁺ + 1) Int.s-29 SC nPrSH nPrS C 260 (M⁺ + 1) Int.s-32 SC iPrSH iPrS C 260 (M⁺ + 1) Int.s-35 SC nBuSH nBuS C 274 (M⁺ + 1) Int.s-38 SC iBuSH iBuS C 274 (M⁺ + 1) Int.s-41 SC 2PhEtSH 2PhEtS C 322 (M⁺ + 1) Int.s-44 SC 4MeOBnSH 4MeOBnS C 322 (M⁺ + 1) Int.s-47 SC 4FBnSH 4FBnS C 326 (M⁺ + 1) Int.s-50 SC 2MeBnSH 2MeBnS C 322 (M⁺ + 1)

Example S-a-1 Synthesis of methyl 3-[3-(naphthalen-2-yl)-4-(4-methylphenylthio)phenyl]propionate (Compound No. N-a-1) (Synthesis method SB)

A solution of Intermediate s-3 (146 mg) in toluene (2 ml) was added with 2-naphthaleneboronic acid (132.3 mg, TCI), 2 M aqueous sodium carbonate (600 μml), methanol (500 μl), and tetrakistriphenylphosphine palladium(0) (henceforth abbreviated as “(Ph₃P)₄Pd”, 38 mg, Nacalai Tesque), and stirred at 80° C. for 14.5 hours. The reaction mixture was added with ethyl acetate (40 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate 4:1) to obtain the title compound (Compound No. S-a-1, 78 mg).

Example S-a-2 Synthesis of 3-[3-(naphthalen-2-yl)-4-(4-methylphenylthio)phenyl]propionic acid (Compound No. S-a-2) (Synthesis method SA)

A solution of the compound of Example S-a-1 (51 mg) in methanol (5.0 ml) was added with 2 N aqueous sodium hydroxide (130 μl), and stirred at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, then made acidic with 5% aqueous hydrochloric acid under ice cooling, and then extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. S-a-2, 47 mg).

Example S-c-1 Synthesis of methyl 3-[4-(4-methoxyphenylthio)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. S-c-1) (Synthesis method SD2)

According to the procedure described in the synthesis method of Intermediate s-6 (Synthesis method), the compound of Example S-b-1 (3.01 g), p-toluenesulfonhydrazide (430.1 mg), and sodium acetate (380.4 mg) were reacted and treated to obtain the title compound (Compound No. S-c-1, 95.1 mg).

Examples S-a-1 to S-a-24, S-b-1 to S-b-138 and S-c-1 to S-c-138

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-S-A-1, Table-S-B-1 to Table-S-B-3 and Table-S-C-1 to Table-S-C-3. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”. The boronic acid reagents shown with the symbols of “BRA (number)” in the columns of “SM2” are those mentioned in Table-Ba-1 and Table-Ba-2.

TABLE S-A

LCMS Exp. Syn SM1 SM2 Rx Y AR method RTime Mass S-a-1 SB Int.s-3 BRA1 4MePh Me 2-Nap C 413 (M⁺ + 1) S-a-2 SA S-a-1 4MePh H 2-Nap C 399 (M⁺ + 1) S-a-3 SB Int.s-3 BRA2 4MePh Me 5-Ind C 402 (M⁺ + 1) S-a-4 SA S-a-3 4MePh H 5-Ind C 388 (M⁺ + 1) S-a-5 SB Int.s-3 BRA3 4MePh Me 1Me-5-Ind C 416 (M⁺ + 1) S-a-6 SA S-a-5 4MePh H 1Me-5-Ind C 402 (M⁺ + 1) S-a-7 SB Int.s-3 BRA4 4MePh Me 1Et-5-Ind C 430 (M⁺ + 1) S-a-8 SA S-a-1 4MePh H 1Et-5-Ind C 416 (M⁺ + 1) S-a-9 SB Int.s-3 BRA5 4MePh Me 5-1HIdz C 403 (M⁺ + 1) S-a-10 SA S-a-9 4MePh H 5-1HIdz C 389 (M⁺ + 1) S-a-11 SB Int.s-3 BRA6 4MePh Me 1Me-5-1HIdz C 417 (M⁺ + 1) S-a-12 SA S-a-11 4MePh H 1Me-5-1HIdz C 403 (M⁺ + 1) S-a-13 SB Int.s-3 BRA7 4MePh Me 1Et-5-1HIdz C 431 (M⁺ + 1) S-a-14 SA S-a-13 4MePh H 1Et-S-1HIdz C 417 (M⁺ + 1) S-a-15 SB Int.s-3 BRA8 4MePh Me 2Me-5-2HIdz C 417 (M⁺ + 1) S-a-16 SA S-a-15 4MePh H 2Me-5-2HIdz C 403 (M⁺ + 1) S-a-17 SB Int.s-3 BRA9 4MePh Me 5-Bzt C 420 (M⁺ + 1) S-a-18 SA S-a-17 4MePh H 5-Bzt C 406 (M⁺ + 1) S-a-19 SB Int.s-3 BRA10 4MePh Me 3-Qu C 414 (M⁺ + 1) S-a-20 SA S-a-19 4MePh H 3-Qu C 400 (M⁺ + 1) S-a-21 SB Int.s-3 BRA11 4MePh Me 6-Qu C 414 (M⁺ + 1) S-a-22 SA S-a-21 4MePh H 6-Qu C 400 (M⁺ + 1) S-a-23 SB Int.s-3 BRA12 4MePh Me 6-IQ C 414 (M⁺ + 1) S-a-24 SA N-a-23 4MePh H 6-IQ C 400 (M⁺ + 1)

TABLE S-B

LCMS Exp. Syn SM1 SM2 Rx Y AR method RTime Mass S-b-1 SB Int.s-5 BRA1 4MeOPh Me 2-Nap C 427 (M⁺ + 1) S-b-2 SA S-b-1 4MeOPh H 2-Nap C 413 (M⁺ + 1) S-b-3 SB Int.s-5 BRA2 4MeOPh Me 5-Ind C 416 (M⁺ + 1) S-b-4 SA S-b-3 4MeOPh H 5-Ind C 402 (M⁺ + 1) S-b-5 SB Int.s-5 BRA3 4MeOPh Me 1Me-5-Ind C 430 (M⁺ + 1) S-b-6 SA S-b-5 4MeOPh H 1Me-5-Ind C 417 (M⁺ + 1) S-b-7 SB Int.s-5 BRA4 4MeOPh Me 1Et-5-Ind C 444 (M⁺ + 1) S-b-8 SA S-b-7 4MeOPh H 1Et-5-Ind C 430 (M⁺ + 1) S-b-9 SB Int.s-5 BRA5 4MeOPh Me 5-1HIdz C 417 (M⁺ + 1) S-b-10 SA S-b-9 4MeOPh H 5-1HIdz C 403 (M⁺ + 1) S-b-11 SB Int.s-5 BRA6 4MeOPh Me 1Me-5-1HIdz C 431 (M⁺ + 1) S-b-12 SA S-b-11 4MeOPh H 1Me-5-1HIdz C 417 (M⁺ + 1) S-b-13 SB Int.s-5 BRA7 4MeOPh Me 1Et-5-1HIdz C 445 (M⁺ + 1) S-b-14 SA S-b-13 4MeOPh H 1Et-5-1HIdz C 431 (M⁺ + 1) S-b-15 SB Int.s-5 BRA8 4MeOPh Me 2Me-5-2HIdz C 431 (M⁺ + 1) S-b-16 SA S-b-15 4MeOPh H 2Me-5-2HIdz C 417 (M⁺ + 1) S-b-17 SB Int.s-5 BRA9 4MeOPh Me 5-Bzt C 434 (M⁺ + 1) S-b-18 SA S-b-17 4MeOPh H 5-Bzt C 420 (M⁺ + 1) S-b-19 SB Int.s-5 BRA10 4MeOPh Me 3-Qu C 428 (M⁺ + 1) S-b-20 SA S-b-19 4MeOPh H 3-Qu C 414 (M⁺ + 1) S-b-21 SB Int.s-5 BRA11 4MeOPh Me 6-Qu C 428 (M⁺ + 1) S-b-22 SA S-b-21 4MeOPh H 6-Qu C 414 (M⁺ + 1) S-b-23 SB Int.s-5 BRA12 4MeOPh Me 6-IQ C 428 (M⁺ + 1) S-b-24 SA S-b-23 4MeOPh H 6-IQ C 414 (M⁺ + 1) S-b-25 SB Int.s-7 BRA1 2MeOPh Me 2-Nap C 427 (M⁺ + 1) S-b-26 SA S-b-25 2MeQPh H 2-Nap C 413 (M⁺ + 1) S-b-27 SB Int.s-7 BRA2 2MeOPh Me 5-Ind C 416 (M⁺ + 1) S-b-28 SA S-b-27 2MeOPh H 5-Ind C 402 (M⁺ + 1) S-b-29 SB Int.s-7 BRA5 2MeOPh Me 5-1HIdz C 417 (M⁺ + 1) S-b-30 SA S-b-29 2MeOPh H 5-1HIdz C 403 (M⁺ + 1) S-b-31 SB Int.s-7 BRA10 2MeOPh Me 3-Qu C 428 (M⁺ + 1) S-b-32 SA S-b-31 2MeOPh H 3-Qu C 414 (M⁺ + 1) S-b-33 SB Int.s-9 BRA1 3MeOPh Me 2-Nap C 427 (M⁺ + 1) S-b-34 SA S-b-33 3MeOPh H 2-Nap C 413 (M⁺ + 1) S-b-35 SB Int.s-9 BRA3 3MeOPh Me 1Me-5-Ind C 430 (M⁺ + 1) S-b-36 SA S-b-35 3MeOPh H 1Me-5-Ind C 416 (M⁺ + 1) S-b-37 SB Int.s-9 BRA6 3MeOPh Me 1Me-5-1HIdz C 431 (M⁺ + 1) S-b-38 SA S-b-37 3MeOPh H 1Me-5-1HIdz C 417 (M⁺ + 1) S-b-39 SB Int.s-9 BRA11 3MeOPh Me 6-Qu C 428 (M⁺ + 1) S-b-40 SA S-b-39 3MeOPh H 6-Qu C 414 (M⁺ + 1) S-b-41 SB Int.s-11 BRA2 2MePh Me 5-Ind C 400 (M⁺ + 1) S-b-42 SA S-b-41 2MePh H 5-Ind C 386 (M⁺ + 1) S-b-43 SB Int.s-11 BRA3 2MePh Me 1Me-5-Ind C 414 (M⁺ + 1) S-b-44 SA S-b-43 2MePh H 1Me-5-Ind C 400 (M⁺ + 1) S-b-45 SB Int.s-11 BRA5 2MePh Me 5-1HIdz C 401 (M⁺ + 1) S-b-46 SA S-b-45 2MePh H 5-1HIdz C 387 (M⁺ + 1) S-b-47 SB Int.s-13 BRA3 3MePh Me 1Me-5-Ind C 414 (M⁺ + 1) S-b-48 SA N-b-47 3MePh H 1Me-5-Ind C 400 (M⁺ + 1) S-b-49 SB Int.s-13 BRA6 3MePh Me 1Me-5-IHIdz C 415 (M⁺ + 1) S-b-50 SA N-b-49 3MePh H 1Me-5-1HIdz C 401 (M⁺ + 1) S-b-51 SB Int.s-13 BRA9 3MePh Me 5-Bzt C 418 (M⁺ + 1) S-b-52 SA N-b-51 3MePh H 5-Bzt C 404 (M⁺ + 1) S-b-53 SB Int.s-15 BRA1 4MePh Me 2-Nap C 411 (M⁺ + 1) S-b-54 SA N-b-53 4MePh H 2-Nap C 397 (M⁺ + 1) S-b-55 SB Int.s-15 BRA2 4MePh Me 5-Ind C 400 (M⁺ + 1) S-b-56 SA N-b-55 4MePh H 5-Ind C 386 (M⁺ + 1) S-b-57 SB Int.s-15 BRA3 4MePh Me 1Me-5-Ind C 418 (M⁺ + 1) S-b-58 SA N-b-57 4MePh H 1Me-5-Ind C 404 (M⁺ + 1) S-b-59 SB Int.s-17 BRA5 2FPh Me 5-1HIdz C 404 (M⁺ + 1) S-b-60 SA N-b-59 2FPh H 5-1HIdz C 390 (M⁺ + 1) S-b-61 SB Int.s-17 BRA6 2FPh Me 1Me-5-Ind C 418 (M⁺ + 1) S-b-62 SA N-b-61 2FPh H 1Me-5-Ind C 404 (M⁺ + 1) S-b-63 SB Int.s-17 BRA11 2FPh Me 6-Qu C 415 (M⁺ + 1) S-b-64 SA N-b-63 2FPh H 6-Qu C 401 (M⁺ + 1) S-b-65 SB Int.s-19 BRA1 3FPh Me 2-Nap C 415 (M⁺ + 1) S-b-66 SA N-b-65 3FPh H 2-Nap C 401 (M⁺ + 1) S-b-67 SB Int.s-19 BRA2 3FPh Me 5-Ind C 403 (M⁺ + 1) S-b-68 SA N-b-67 3FPh H 5-Ind C 389 (M⁺ + 1) S-b-69 SB Int.s-19 BRA6 3FPh Me 1Me-5-1HIdz C 418 (M⁺ + 1) S-b-70 SA N-b-69 3FPh H 1Me-5-1HIdz C 404 (M⁺ + 1) S-b-71 SB Int.s-21 BRA3 4FPh Me 1Me-5-Ind C 418 (M⁺ + 1) S-b-72 SA N-b-71 4FPh H 1Me-5-Ind C 404 (M⁺ + 1) S-b-73 SB Int.s-21 BRA5 4FPh Me 5-1HIdz C 404 (M⁺ + 1) S-b-74 SA N-b-73 4FPh H 5-1HIdz C 390 (M⁺ + 1) S-b-75 SB Int.s-21 BRA10 4FPh Me 3-Qu C 415 (M⁺ + 1) S-b-76 SA N-b-75 4FPh H 3-Qu C 401 (M⁺ + 1) S-b-77 SB Int.s-24 BRA1 cPen Me 2-Nap C 389 (M⁺ + 1) S-b-78 SA N-b-77 cPen H 2-Nap C 375 (M⁺ + 1) S-b-79 SB Int.s-24 BRA2 cPen Me 5-Ind C 378 (M⁺ + 1) S-b-80 SA N-b-79 cPen H 5-Ind C 364 (M⁺ + 1) S-b-81 SB Int.s-24 BRA6 cPen Me 1Me-5-1HIdz C 407 (M⁺ + 1) S-b-82 SA N-b-81 cPen H 1Me-5-1HIdz C 393 (M⁺ + 1) S-b-83 SB Int.s-27 BRA3 cHex Et 1Me-5-Ind C 406 (M⁺ + 1) S-b-84 SA N-b-83 cHex H 1Me-5-Ind C 392 (M⁺ + 1) S-b-85 SB Int.s-27 BRA5 cHex Et 5-1HIdz C 393 (M⁺ + 1) S-b-86 SA N-b-85 cHex H 5-1HIdz C 379 (M⁺ + 1) S-b-87 SB Int.s-27 BRA12 cHex Et 6-Qu C 363 (M⁺ + 1) S-b-88 SA N-b-87 cHex H 6-Qu C 349 (M⁺ + 1) S-b-89 SB Int.s-30 BRA12 nPr Et 2-Nap C 362 (M⁺ + 1) S-b-90 SA N-b-89 nPr H 2-Nap C 348 (M⁺ + 1) S-b-91 SB Int.s-30 BRA2 nPr Et 5-Ind C 351 (M⁺ + 1) S-b-92 SA N-b-91 nPr H 5-Ind C 337 (M⁺ + 1) S-b-93 SB Int.s-30 BRA6 nPr Et 1Me-5-1HIdz C 366 (M⁺ + 1) S-b-94 SA N-b-93 nPr H 1Me-5-1HIdz C 352 (M⁺ + 1) S-b-95 SB Int.s-33 BRA1 iPr Et 2-Nap C 362 (M⁺ + 1) S-b-96 SA N-b-95 iPr H 2-Nap C 348 (M⁺ + 1) S-b-97 SB Int.s-33 BRA3 iPr Et 1Me-5-Ind C 365 (M⁺ + 1) S-b-98 SA N-b-97 iPr H 1Me-5-Ind C 351 (M⁺ + 1) S-b-99 SB Int.s-33 BRA5 iPr Et 5-1HIdz C 352 (M⁺ + 1) S-b-100 SA N-b-99 iPr H 5-1HIdz C 338 (M⁺ + 1) S-b-101 SB Int.s-36 BRA2 nBu Et 5-Ind C 366 (M⁺ + 1) S-b-102 SA N-b-101 nBu H 5-Ind C 352 (M⁺ + 1) S-b-103 SB Int.s-36 BRA5 nBu Et 5-1HIdz C 366 (M⁺ + 1) S-b-104 SA N-b-103 nBu H 5-1HIdz C 352 (M⁺ + 1) S-b-105 SB Int.s-36 BRA11 nBu Et 6-Qu C 378 (M⁺ + 1) S-b-106 SA N-b-105 nBu H 6-Qu C 364 (M⁺ + 1) S-b-107 SB Int.s-39 BRA1 iBu Me 2-Nap C 377 (M⁺ + 1) S-b-108 SA N-b-107 iBu H 2-Nap C 363 (M⁺ + 1) S-b-109 SB Int.s-39 BRA3 iBu Me 1Me-5-Ind C 380 (M⁺ + 1) S-b-110 SA N-b-109 iBu H 1Me-5-Ind C 366 (M⁺ + 1) S-b-111 SB Int.s-39 BRA5 iBu Me 5-1HIdz C 366 (M⁺ + 1) S-b-112 SA N-b-111 iBu H 5-1HIdz C 352 (M⁺ + 1) S-b-113 SB Int.s-39 BRA6 iBu Me 1Me-5-1HIdz C 381 (M⁺ + 1) S-b-114 SA N-b-113 iBu H 1Me-5-1HIdz C 367 (M⁺ + 1) S-b-115 SB Int.s-42 BRA1 PhEt Me 2-Nap C 425 (M⁺ + 1) S-b-116 SA N-b-115 PhEt H 2-Nap C 411 (M⁺ + 1) S-b-117 SB Int.s-42 BRA2 PhEt Me 5-Ind C 414 (M⁺ + 1) S-b-118 SA N-b-117 PhEt H 5-Ind C 400 (M⁺ + 1) S-b-119 SB Int.s-42 BRA3 PhEt Me 1Me-5-Ind C 428 (M⁺ + 1) S-b-120 SA N-b-119 PhEt H 1Me-5-Ind C 414 (M⁺ + 1) S-b-121 SB Int.s-45 BRA1 4MeOBn Et 2-Nap C 441 (M⁺ + 1) S-b-122 SA N-b-121 4MeOBn H 2-Nap C 427 (M⁺ + 1) S-b-123 SB Int.s-45 BRA5 4MeOBn Et 5-1HIdz C 431 (M⁺ + 1) S-b-124 SA N-b-123 4MeOBn H 5-1HIdz C 417 (M⁺ + 1) S-b-125 SB Int.s-45 BRA6 4MeOBn Et 1Me-5-1HIdz C 431 (M⁺ + 1) S-b-126 SA N-b-125 4MeOBn H 1Me-5-1HIdz C 417 (M⁺ + 1) S-b-127 SB Int.s-48 BRA1 4FBn Et 2-Nap C 429 (M⁺ + 1) S-b-128 SA N-b-127 4FBn H 2-Nap C 415 (M⁺ + 1) S-b-129 SB Int.s-48 BRA2 4FBn Et 5-Ind C 418 (M⁺ + 1) S-b-130 SA N-b-129 4FBn H 5-Ind C 404 (M⁺ + 1) S-b-131 SB Int.s-48 BRA6 4FBn Et 1Me-5-1HIdz C 418 (M⁺ + 1) S-b-132 SA N-b-131 4FBn H 1Me-5-1HIdz C 404 (M⁺ + 1) S-b-133 SB Int.s-51 BRA3 2MeBn Et 1Me-5-Ind C 428 (M⁺ + 1) S-b-134 SA N-b-133 2MeBn H 1Me-5-Ind C 414 (M⁺ + 1) S-b-135 SB Int.s-51 BRA5 2MeBn Et 5-1HIdz C 415 (M⁺ + 1) S-b-136 SA N-b-135 2MeBn H 5-1HIdz C 401 (M⁺ + 1) S-b-137 SB Int.s-51 BRA10 2MeBn Et 3-Qu C 426 (M⁺ + 1) S-b-138 SA N-b-137 2MeBn H 3-Qu C 412 (M⁺ + 1)

TABLE S-C

LCMS Exp. Syn SM1 SM2 Rx Y AR method RTime Mass S-c-1 SB Int.s-6 BRA1 4MeOPh Me 2-Nap C 429 (M⁺ + 1) S-c-2 SA S-c-1 4MeOPh H 2-Nap C 415 (M⁺ + 1) S-c-3 SB Int.s-6 BRA2 4MeOPh Me 5-Ind C 418 (M⁺ + 1) S-c-4 SA S-c-3 4MeOPh H 5-Ind C 404 (M⁺ + 1) S-c-5 SB Int.s-6 BRA3 4MeOPh Me 1Me-5-Ind C 432 (M⁺ + 1) S-c-6 SA S-c-5 4MeOPh H 1Me-5-Ind C 418 (M⁺ + 1) S-c-7 SB Int.s-6 BRA4 4MeOPh Me 1Et-5-Ind C 446 (M⁺ + 1) S-c-8 SA S-c-7 4MeOPh H 1Et-5-Ind C 432 (M⁺ + 1) S-c-9 SB Int.s-6 BRA5 4MeOPh Me 5-1HIdz C 419 (M⁺ + 1) S-c-10 SA S-c-9 4MeOPh H 5-1HIdz C 405 (M⁺ + 1) S-c-11 SB Int.s-6 BRA6 4MeOPh Me 1Me-5-1HIdz C 433 (M⁺ + 1) S-c-12 SA S-c-11 4MeOPh H 1Me-5-1HIdz C 419 (M⁺ + 1) S-c-13 SB Int.s-6 BRA7 4MeOPh Me 1Et-5-1HIdz C 447 (M⁺ + 1) S-c-14 SA S-c-13 4MeOPh H 1Et-5-1HIdz C 433 (M⁺ + 1) S-c-15 SB Int.s-6 BRA8 4MeOPh Me 2Me-5-2HIdz C 433 (M⁺ + 1) S-c-16 SA S-c-15 4MeOPh H 2Me-5-2HIdz C 419 (M⁺ + 1) S-c-17 SB Int.s-6 BRA9 4MeOPh Me 5-Bzt C 436 (M⁺ + 1) S-c-18 SA S-c-17 4MeOPh H 5-Bzt C 422 (M⁺ + 1) S-c-19 SB Int.s-6 BRA10 4MeOPh Me 3-Qu C 430 (M⁺ + 1) S-c-20 SA S-c-19 4MeOPh H 3-Qu C 416 (M⁺ + 1) S-c-21 SB Int.s-6 BRA11 4MeOPh Me 6-Qu C 430 (M⁺ + 1) S-c-22 SA S-c-21 4MeOPh H 6-Qu C 416 (M⁺ + 1) S-c-23 SB Int.s-6 BRA12 4MeOPh Me 6-IQ C 430 (M⁺ + 1) S-c-24 SA S-c-23 4MeOPh H 6-IQ C 416 (M⁺ + 1) S-c-25 SB Int.s-8 BRA1 2MeOPh Me 2-Nap C 429 (M⁺ + 1) S-c-26 SA S-c-25 2MeOPh H 2-Nap C 415 (M⁺ + 1) S-c-27 SB Int.s-8 BRA3 2MeOPh Me 1Me-5-Ind C 431 (M⁺ + 1) S-c-28 SA S-c-27 2MeOPh H 1Me-5-Ind C 418 (M⁺ + 1) S-c-29 SB Int.s-8 BRA5 2MeOPh Me 5-1-HIdz C 419 (M⁺ + 1) S-c-30 SA S-c-29 2MeOPh H 5-1-HIdz C 405 (M⁺ + 1) S-c-31 SB Int.s-8 BRA10 2MeOPh Me 3-Qu C 430 (M⁺ + 1) S-c-32 SA S-c-31 2MeOPh H 3-Qu C 416 (M⁺ + 1) S-c-33 SB Int.s-10 BRA1 3MeOPh Me 2-Nap C 429 (M⁺ + 1) S-c-34 SA S-c-33 3MeOPh H 2-Nap C 415 (M⁺ + 1) S-c-35 SB Int.s-10 BRA2 3MeOPh Me 5-Ind C 418 (M⁺ + 1) S-c-36 SA S-c-35 3MeOPh H 5-Ind C 403 (M⁺ + 1) S-c-37 SB Int.s-10 BRA5 3MeOPh Me 1Me-5-1HIdz C 433 (M⁺ + 1) S-c-38 SA S-c-37 3MeOPh H 1Me-5-1HIdz C 419 (M⁺ + 1) S-c-39 SB Int.s-10 BRA11 3MeOPh Me 6-Qu C 430 (M⁺ + 1) S-c-40 SA S-c-39 3MeOPh H 6-Qu C 416 (M⁺ + 1) S-c-41 SB Int.s-12 BRA3 2MePh Me 1Me-5-Ind C 402 (M⁺ + 1) S-c-42 SA S-c-41 2MePh H 1Me-5-Ind C 388 (M⁺ + 1) S-c-43 SB Int.s-12 BRA5 2MePh Me 5-1HIdz C 416 (M⁺ + 1) S-c-44 SA S-c-43 2MePh H 5-1HIdz C 402 (M⁺ + 1) S-c-45 SB Int.s-12 BRA6 2MePh Me 1-Me-5-1HIdz C 417 (M⁺ + 1) S-c-46 SA S-c-45 2MePh H 1-Me-5-1HIdz C 403 (M⁺ + 1) S-c-47 SB Int.s-14 BRA3 3MePh Me 1-Me-5-Ind C 416 (M⁺ + 1) S-c-48 SA N-c-47 3MePh H 1-Me-5-Ind C 402 (M⁺ + 1) S-c-49 SB Int.s-14 BRA6 3MePh Me 1-Me-5-1HIdz C 417 (M⁺ + 1) S-c-50 SA N-c-49 3MePh H 1-Me-5-1HIdz C 403 (M⁺ + 1) S-c-51 SB Int.s-14 BRA9 3MePh Me 5Bzt C 420 (M⁺ + 1) S-c-52 SA N-c-51 3MePh H 5Bzt C 406 (M⁺ + 1) S-c-53 SB Int.s-16 BRA1 4MePh Me 2-Nap C 413 (M⁺ + 1) S-c-54 SA N-c-53 4MePh H 2-Nap C 399 (M⁺ + 1) S-c-55 SB Int.s-16 BRA2 4MePh Me 5-Ind C 402 (M⁺ + 1) S-c-56 SA N-c-55 4MePh H 5-Ind C 388 (M⁺ + 1) S-c-57 SB Int.s-16 BRA3 4MePh Me 1Me-5-Ind C 420 (M⁺ + 1) S-c-58 SA N-c-57 4MePh H 1Me-5-Ind C 406 (M⁺ + 1) S-c-59 SB Int.s-18 BRA5 2FPh Me 5-1HIdz C 406 (M⁺ + 1) S-c-60 SA N-c-59 2FPh H 5-1HIdz C 392 (M⁺ + 1) S-c-61 SB Int.s-18 BRA6 2FPh Me 1Me-5-1HInd C 420 (M⁺ + 1) S-c-62 SA N-c-61 2FPh H 1Me-5-1HInd C 406 (M⁺ + 1) S-c-63 SB Int.s-18 BRA11 2FPh Me 6-Qu C 418 (M⁺ + 1) S-c-64 SA N-c-63 2FPh H 6-Qu C 404 (M⁺ + 1) S-c-65 SB Int.s-20 BRA1 3FPh Me 2-Nap C 417 (M⁺ + 1) S-c-66 SA N-c-65 3FPh H 2-Nap C 403 (M⁺ + 1) S-c-67 SB Int.s-20 BRA2 3FPh Me 5-Ind C 405 (M⁺ + 1) S-c-68 SA N-c-67 3FPh H 5-Ind C 391 (M⁺ + 1) S-c-69 SB Int.s-20 BRA6 3FPh Me 1Me-5-1HIdz C 421 (M⁺ + 1) S-c-70 SA N-c-69 3FPh H 1Me-5-1HIdz C 407 (M⁺ + 1) S-c-71 SB Int.s-22 BRA3 4FPh Me 1Me-5-Ind C 420 (M⁺ + 1) S-c-72 SA N-c-71 4FPh H 1Me-5-Ind C 406 (M⁺ + 1) S-c-73 SB Int.s-22 BRA5 4FPh Me 5-1HIdz C 406 (M⁺ + 1) S-c-74 SA N-c-73 4FPh H 5-1HIdz C 392 (M⁺ + 1) S-c-75 SB Int.s-22 BRA10 4FPh Me 3-Qu C 418 (M⁺ + 1) S-c-76 SA N-c-75 4FPh H 3-Qu C 404 (M⁺ + 1) S-c-77 SB Int.s-25 BRA1 cPen Et 2-Nap C 391 (M⁺ + 1) S-c-78 SA N-c-77 cPen H 2-Nap C 377 (M⁺ + 1) S-c-79 SB Int.s-25 BRA2 cPen Et 5-Ind C 380 (M⁺ + 1) S-c-80 SA N-c-79 cPen H 5-Ind C 366 (M⁺ + 1) S-c-81 SB Int.s-25 BRA6 cPen Et 1Me-5-1HIdz C 409 (M⁺ + 1) S-c-82 SA N-c-81 cPen H 1Me-5-1HIdz C 395 (M⁺ + 1) S-c-83 SB Int.s-28 BRA3 cHex Et 1Me-5-Ind C 408 (M⁺ + 1) S-c-84 SA N-c-83 cHex H 1Me-5-Ind C 394 (M⁺ + 1) S-c-85 SB Int.s-28 BRA5 cHex Et 5-1HIdz C 395 (M⁺ + 1) S-c-86 SA N-c-85 cHex H 5-1HIdz C 381 (M⁺ + 1) S-c-87 SB Int.s-28 BRA12 cHex Et 6-Qu C 365 (M⁺ + 1) S-c-88 SA N-c-87 cHex H 6-Qu C 351 (M⁺ + 1) S-c-89 SB Int.s-31 BRA1 nPr Et 2-Nap C 365 (M⁺ + 1) S-c-90 SA N-c-89 nPr H 2-Nap C 351 (M⁺ + 1) S-c-91 SB Int.s-31 BRA2 nPr Et 5-Ind C 353 (M⁺ + 1) S-c-92 SA N-c-91 nPr H 5-Ind C 339 (M⁺ + 1) S-c-93 SB Int.s-31 BRA6 nPr Et 1Me-5-1HIdz C 368 (M⁺ + 1) S-c-94 SA N-c-93 nPr H 1Me-5-1HIdz C 354 (M⁺ + 1) S-c-95 SB Int.s-34 BRA3 iPr Et 1Me-5-Ind C 368 (M⁺ + 1) S-c-96 SA N-c-95 iPr H 1Me-5-Ind C 354 (M⁺ + 1) S-c-97 SB Int.s-34 BRA5 iPr Et 5-1HIdz C 354 (M⁺ + 1) S-c-98 SA N-c-97 iPr H 5-1HIdz C 340 (M⁺ + 1) S-c-99 SB Int.s-34 BRA12 iPr Et 6-IQ C 380 (M⁺ + 1) S-c-100 SA N-c-99 iPr H 6-IQ C 366 (M⁺ + 1) S-c-101 SB Int.s-37 BRA1 nBu Et 2-Nap C 379 (M⁺ + 1) S-c-102 SA N-c-101 nBu H 2-Nap C 365 (M⁺ + 1) S-c-103 SB Int.s-37 BRA2 nBu Et 5-Ind C 368 (M⁺ + 1) S-c-104 SA N-c-103 nBu H 5-Ind C 354 (M⁺ + 1) S-c-105 SB Int.s-37 BRA6 nBu Et 1Me-5-1HIdz C 383 (M⁺ + 1) S-c-106 SA N-c-105 nBu H 1Me-5-1HIdz C 369 (M⁺ + 1) S-c-107 SB Int.s-40 BRA1 iBu Et 2-Nap C 379 (M⁺ + 1) S-c-108 SA N-c-107 iBu H 2-Nap C 365 (M⁺ + 1) S-c-109 SB Int.s-40 BRA3 iBu Et 1Me-5-Ind C 382 (M⁺ + 1) S-c-110 SA N-c-109 iBu H 1Me-5-Ind C 368 (M⁺ + 1) S-c-111 SB Int.s-40 BRA5 iBu Et 5-1HIdz C 369 (M⁺ + 1) S-c-112 SA N-c-111 iBu H 5-1HIdz C 355 (M⁺ + 1) S-c-113 SB Int.s-40 BRA6 iBu Et 1Me-5-1HIdz C 383 (M⁺ + 1) S-c-114 SA N-c-113 iBu H 1Me-5-1HIdz C 369 (M⁺ + 1) S-c-115 SB Int.s-43 BRA1 PhEt Et 2-Nap C 427 (M⁺ + 1) S-c-116 SA N-c-115 PhEt H 2-Nap C 413 (M⁺ + 1) S-c-117 SB Int.s-43 BRA2 PhEt Et 5-Ind C 416 (M⁺ + 1) S-c-118 SA N-c-117 PhEt H 5-Ind C 402 (M⁺ + 1) S-c-119 SB Int.s-43 BRA6 PhEt Et 1Me-5-1HIdz C 431 (M⁺ + 1) S-c-120 SA N-c-119 PhEt H 1Me-5-1HIdz C 417 (M⁺ + 1) S-c-121 SB Int.s-46 BRA1 4MeOBn Et 2-Nap C 443 (M⁺ + 1) S-c-122 SA N-c-121 4MeOBn H 2-Nap C 429 (M⁺ + 1) S-c-123 SB Int.s-46 BRA3 4MeOBn Et 1Me-5-Ind C 446 (M⁺ + 1) S-c-124 SA N-c-123 4MeOBn H 1Me-5-Ind C 432 (M⁺ + 1) S-c-125 SB Int.s-46 BRA5 4MeOBn Et 5-1HIdz C 419 (M⁺ + 1) S-c-126 SA N-c-125 4MeOBn H 5-1HIdz C 405 (M⁺ + 1) S-c-127 SB Int.s-49 BRA1 4FBn Et 2-Nap C 431 (M⁺ + 1) S-c-128 SA N-c-127 4FBn H 2-Nap C 417 (M⁺ + 1) S-c-129 SB Int.s-49 BRA2 4FBn Et 5-Ind C 420 (M⁺ + 1) S-c-130 SA N-c-129 4FBn H 5-Ind C 406 (M⁺ + 1) S-c-131 SB Int.s-49 BRA5 4FBn Et 5-1HIdz C 406 (M⁺ + 1) S-c-132 SA N-c-131 4FBn H 5-1HIdz C 392 (M⁺ + 1) S-c-133 SB Int.s-52 BRA3 2MeBn Et 1Me-5-Ind C 430 (M⁺ + 1) S-c-134 SA N-c-133 2MeBn H 1Me-5-Ind C 416 (M⁺ + 1) S-c-135 SB Int.s-52 BRA6 2MeBn Et 1Me-5-1HIdz C 431 (M⁺ + 1) S-c-136 SA N-c-135 2MeBn H 1Me-5-1HIdz C 417 (M⁺ + 1) S-c-137 SB Int.s-52 BRA11 2MeBn Et 6-Qu C 428 (M⁺ + 1) S-c-138 SA N-c-137 2MeBn H 6-Qu C 414 (M⁺ + 1)

Example S-d-1 Synthesis of ethyl 3-{4-[(4-methoxyphenyl)methylsulfinyl]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. S-d-1) (Synthesis method SG)

A solution of the compound of Example S-c-121 (130.9 mg) in dichloromethane (4 ml) was added with 3-chloroperoxybenzoic acid (60.0 mg, TCI), and stirred at room temperature for 1.5 hours. The reaction mixture was added with water (10 ml), extracted with dichloromethane (20 ml), and then washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, chloroform:methanol=30:1) to obtain the title compound (Compound No. S-d-1, 108.7 mg).

Example S-d-7 Synthesis of ethyl 3-{4-[(4-methoxyphenyl)methylsulfonyl]-3-(naphthalen-2-yl)phenyl}propionate (Compound No. S-d-7) (Synthesis method SG)

A solution of the compound of Example S-c-121 (53.1 mg) in dichloromethane (3 ml) was added with 3-chloroperoxybenzoic acid (74.5 mg, TCI), and stirred at room temperature for 5 hours. The reaction mixture was added with water (10 ml), extracted with dichloromethane (20 ml), and then washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. S-d-7, 48.1 mg).

Examples S-d-1 to S-d-36

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-S-D-1. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, and the starting compounds 1 are mentioned in the columns of “SM1”.

TABLE S-D

LCMS Exp. Syn SM1 RS(O)n Y AR method RTime Mass S-d-1 SG S-c-121 4MeOBnSO Et 2-Nap C 473 (M⁺ + 1) S-d-2 SA S-d-1 4MeOBnSO H 2-Nap C 445 (M⁺ + 1) S-d-3 SG S-c-123 4MeOBnSO Et 1Me-5-Ind C 476 (M⁺ + 1) S-d-4 SA S-d-3 4MeOBnSO H 1Me-5-Ind C 448 (M⁺ + 1) S-d-5 SG S-c-125 4MeOBnSO Et 5-1HIdz C 463 (M⁺ + 1) S-d-6 SA S-d-5 4MeOBnSO H 5-1HIdz C 435 (M⁺ + 1) S-d-7 SG S-c-121 4MeOBnSO2 Et 2-Nap C 489 (M⁺ + 1) S-d-8 SA S-d-7 4MeOBnSO2 H 2-Nap C 461 (M⁺ + 1) S-d-9 SG S-c-123 4MeOBnSO2 Et 1Me-5-Ind C 492 (M⁺ + 1) S-d-10 SA S-d-9 4MeOBnSO2 H 1Me-5-Ind C 464 (M⁺ + 1) S-d-11 SG S-c-125 4MeOBnSO2 Et 5-1HIdz C 479 (M⁺ + 1) S-d-12 SA S-d-11 4MeOBnSO2 H 5-1HIdz C 451 (M⁺ + 1) S-d-13 SG S-c-77 cPenSO Et 2-Nap C 421 (M⁺ + 1) S-d-14 SA S-d-13 cPenSO H 2-Nap C 393 (M⁺ + 1) S-d-15 SG S-c-79 cPenSO Et 5-Ind C 410 (M⁺ + 1) S-d-16 SA S-d-15 cPenSO H 5-Ind C 381 (M⁺ + 1) S-d-17 SG S-c-81 cPenSO Et 1Me-5-1HIdz C 425 (M⁺ + 1) S-d-18 SA S-d-17 cPenSO H 1Me-5-1HIdz C 397 (M⁺ + 1) S-d-19 SG S-c-77 cPenSO2 Et 2-Nap C 437 (M⁺ + 1) S-d-20 SA S-d-19 cPenSO2 H 2-Nap C 409 (M⁺ + 1) S-d-21 SG S-c-79 cPenSO2 Et 5-Ind C 426 (M⁺ + 1) S-d-22 SA S-d-21 cPenSO2 H 5-Ind C 397 (M⁺ + 1) S-d-23 SG S-c-81 cPenSO2 Et 1Me-5-1HIdz C 441 (M⁺ + 1) S-d-24 SA S-d-23 cPenSO2 H 1Me-5-1HIdz C 413 (M⁺ + 1) S-d-25 SG S-c-101 nBuSO Et 2-Nap C 409 (M⁺ + 1) S-d-26 SA S-d-25 nBuSO H 2-Nap C 377 (M⁺ + 1) S-d-27 SQ S-c-103 nBuSO Et 5-Ind C 398 (M⁺ + 1) S-d-28 SA S-d-27 nBuSO H 5-Ind C 365 (M⁺ + 1) S-d-29 SG S-c-105 nBuSO Et 1Me-5-1HIdz C 413 (M⁺ + 1) S-d-30 SA S-d-29 nBuSO H 1Me-5-1HIdz C 381 (M⁺ + 1) S-d-31 SG S-c-101 nBuSO2 Et 2-Nap C 425 (M⁺ + 1) S-d-32 SA S-d-31 nBuSO2 H 2-Nap C 397 (M⁺ + 1) S-d-33 SG S-c-103 nBuSO2 Et 5-Ind C 410 (M⁺ + 1) S-d-34 SA S-d-33 nBuSO2 H 5-Ind C 385 (M⁺ + 1) S-d-35 SG S-c-105 nBuSO2 Et 1Me-5-1HIdz C 425 (M⁺ + 1) S-d-36 SA S-d-35 nBuSO2 H 1Me-5-1HIdz C 401 (M⁺ + 1)

Reference Examples Intermediates An-1 to An-5 Synthesis of ethyl 3-[2-hydroxy-3-(naphthalen-2-yl)pyridin-5-yl]propionate (Intermediate Ah-1)

A solution of the compound of Example P-42 (452 mg) in a mixture of ethyl acetate (5 ml) and methanol (2.5 ml) was added with 10% palladium/carbon (50 mg), and stirred at room temperature for 2 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate Ah-1,321 mg). Mass (FAB): 322 (M⁺+1).

Synthesis of ethyl 3-[3-(naphthalen-2-yl)-2-(trifluoromethanesulfonyl)pyridin-5-yl]propionate (Intermediate An-1)

According to the procedure described in the synthesis method of Intermediate Aa-1, Intermediate Ah-1 (310 mg) and trifluoromethanesulfonic anhydride (170 μl) were reacted and treated to obtain the title compound (Intermediate An-1, 355 mg). Mass (FAB): 454 (M⁺+1).

Typical examples of the reaction intermediates that can be obtained by reacting and treating corresponding starting compounds according to the method described above are shown below.

-   Intermediate An-2: ethyl     3-[3-(1H-indol-5-yl)-2-(trifluoromethanesulfonyl)pyridin-5-yl]propionate -   Intermediate An-3: ethyl     3-[3-(1-methyl-1H-indol-5-yl)-2-(trifluoromethanesulfonyl)pyridin-5-yl]propionate -   Intermediate An-4: ethyl     3-[3-(1H-indazol-5-yl)-2-(trifluoromethanesulfonyl)pyridin-5-yl]propionate -   Intermediate An-5: ethyl     3-[3-(1-methyl-1H-indazol-5-yl)-2-(trifluoromethanesulfonyl)pyridin-5-yl]propionate

Examples Cn-1 to Cn-45

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds according to the methods described in Examples Ca-1 and Ca-2 are shown in Table-Cn-1.

In the table, the substances mentioned in the column of “SM1” correspond to reaction intermediates, and the substances mentioned in the column of “SM2” correspond to the boronic acid reagent used in Example Ca-1. The boronic acid reagents indicated with the symbols of “BRA (number)” in the columns of “SM2” are those mentioned in Table-Ba-1 and Table-Ba-2.

TABLE Cn

LCMS Exp. Rx Y AR SM1 SM2 method RTime Mass Cn-1 Ph Et 2-Nap An-1 BRA14 D 382 (M⁺ + 1) Cn-2 Ph H 2-Nap Cn-1 — C 354 (M⁺ + 1) Cn-3 Ph Et 5-Ind An-2 BRA14 C 371 (M⁺ + 1) Cn-4 Ph H 5-Ind Cn-3 — C 343 (M⁺ + 1) Cn-5 Ph Et 1Me-5-Ind An-3 BRA14 C 385 (M⁺ + 1) Cn-6 Ph H 1Me-5-Ind Cn-5 — C 357 (M⁺ + 1) Cn-7 Ph Et 5-1HIdz An-4 BRA14 C 372 (M⁺ + 1) Cn-8 Ph H 5-1HIdz Cn-7 — C 344 (M⁺ + 1) Cn-9 Ph Et 1Me-5-1HIdz An-5 BRA14 C 386 (M⁺ + 1) Cn-10 Ph H 1Me-5-1H1dz Cn-9 — C 358 (M⁺ + 1) Cn-11 4MeOPh H 2-Nap An-1 BRA19 C 384 (M⁺ + 1) Cn-12 4MeOPh H 5-Ind An-2 BRA19 C 384 (M⁺ + 1) Cn-13 4MeOPh H 5-1HIdz An-4 BRA19 C 387 (M⁺ + 1) Cn-14 4MeOPh H 1Me-5-1HIdz An-5 BRA19 C 388 (M⁺ + 1) Cn-15 3MeOPh H 2-Nap An-1 BRA37 C 368 (M⁺ + 1) Cn-16 2MeOPh H 2-Nap An-1 BRA38 C 371 (M⁺ + 1) Cn-17 2MeOPh H 1Me-5-Ind An-3 BRA38 C 372 (M⁺ + 1) Cn-18 2MeOPh H 1Me-5-1HIdz An-5 BRA38 C 388 (M⁺ + 1) Cn-19 2MePh H 2-Nap An-1 BRA59 C 368 (M⁺ + 1) Cn-20 2MePh H 1Me-5-Ind An-3 BRA59 C 381 (M⁺ + 1) Cn-21 2MePh H 1Me-5-1HIdz An-5 BRA59 C 372 (M⁺ + 1) Cn-22 3MePh H 2-Nap An-1 BRA60 C 368 (M⁺ + 1) Cn-23 3MePh H 5-1HIdz An-4 BRA60 C 358 (M⁺ + 1) Cn-24 4MePh H 2-Nap An-1 BRA29 C 368 (M⁺ + 1) Cn-25 4MePh H 5-Ind An-2 BRA29 C 357 (M⁺ + 1) Cn-26 4MePh H 1Me-5-Ind An-3 BRA29 C 371 (M⁺ + 1) Cn-27 4MePh H 5-1-HIdz An-4 BRA29 C 358 (M⁺ + 1) Cn-28 4MePh H 1Me-5-1HIdz An-5 BRA29 C 372 (M⁺ + 1) Cn-29 4CF3Ph H 5-Ind An-2 BRA41 C 411 (M⁺ + 1) Cn-30 4CF3Ph H 5-1HIdz An-4 BRA41 C 412 (M⁺ + 1) Cn-31 4CF3Ph H 1Me-5-1HIdz An-5 BRA41 C 426 (M⁺ + 1) Cn-32 4ClPh H 5-Ind An-2 BRA30 C 377 (M⁺ + 1) Cn-33 4ClPh H 1Me-5-Ind An-3 BRA30 C 391 (M⁺ + 1) Cn-34 4ClPh H 1Me-5-1HIdz An-5 BRA30 C 392 (M⁺ + 1) Cn-35 2FPh H 2-Nap An-1 BRA32 C 372 (M⁺ + 1) Cn-36 2FPh H 1Me-5-Ind An-3 BRA32 C 375 (M⁺ + 1) Cn-37 2FPh H 5-1HIdz An-4 BRA32 C 362 (M⁺ + 1) Cn-38 2FPh H 1Me-5-1HIdz An-5 BRA32 C 376 (M⁺ + 1) Cn-39 3FPh H 5-Ind An-2 BRA33 C 361 (M⁺ + 1) Cn-40 3FPh H 5-1HIdz An-4 BRA33 C 362 (M⁺ + 1) Cn-41 3FPh H 1Me-5-1HIdz An-5 BRA33 C 376 (M⁺ + 1) Cn-42 4FPh H 2-Nap An-1 BRA34 C 372 (M⁺ + 1) Cn-43 4FPh H 5-Ind An-2 BRA34 C 361 (M⁺ + 1) Cn-44 4FPh H 5-1HIdz An-4 BRA34 C 362 (M⁺ + 1) Cn-45 4FPh H 1Me-5-1HIdz An-5 BRA34 C 376 (M⁺ + 1)

Reference Examples Intermediates Int. n-1 to Int. n-115 Synthesis of methyl 3-(4-aminophenyl)propionate (Intermediate Int. n-1) (Synthesis method NL)

A solution obtained beforehand by adding thionyl chloride (6.7 ml, WAKO) dropwise to methanol (50 ml) under ice cooling and mixing them was added dropwise with a solution of 4-aminohydrocinnamic acid (9.97 g, TCI) in methanol (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 16.5 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with ethyl acetate (200 ml), and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate Int. n-1, 13.13 g).

Synthesis of methyl 3-(4-amino-3-bromophenyl)propionate (Intermediate Int. n-2) (Synthesis method NK)

A solution of Intermediate Int. n-1 (9.93 g) in acetic acid (55 ml) was added with potassium bromide (6.60 g, WAKO) and sodium tungstenate(IV) dihydrate (18.23 g, WAKO), stirred for 5 minutes, then added dropwise with aqueous hydrogen peroxide (3.5 ml, WAKO) at 0° C. over 5 minutes, warmed to room temperature, and then stirred for 1 hour. The reaction mixture was poured into 5% aqueous ammonia containing ice, thereby adjusted to pH of about 6, and then added with dichloromethane (200 ml) for extraction. The organic layer was washed successively with saturated aqueous ammonium chloride, saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=3:1) to obtain the title compound (Intermediate Int. n-2, 3.07 g).

Synthesis of methyl 3-(4-benzylamino-3-bromophenyl)propionate (Intermediate Int. n-3) (Synthesis method NC1)

A solution of Intermediate Int. n-2 (10.97 g) in methanol (30 ml) was added with benzaldehyde (5.25 ml, TCI) and anhydrous sodium sulfate (6.49 g, WAKO), and stirred at 60° C. for 13 hours. The reaction mixture was added with sodium cyanotrihydroridoborate (2.73 g, WAKO), and further stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with dichloromethane (150 ml), and the organic layer was washed with saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-3, 13.45 g).

Synthesis of methyl 3-[3-bromo-(4-fluorobenzylamino)phenyl]propionate (Intermediate Int. n-4) (Synthesis method NC2)

A solution of Intermediate Int. n-2 (5.80 g) in dichloromethane (100 ml) was added with p-fluorobenzaldehyde (2.83 ml, TCI), sodium triacetoxyborohydride (7.14 g, Ald) and acetic acid (1.4 ml), and stirred at room temperature for 19 hours. The reaction mixture was extracted with dichloromethane (300 ml), and the organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-4, 7.51 g).

Synthesis of methyl 3-[4-amino-3-(naphthalen-2-yl)phenyl]propionate (Intermediate Int. n-7) (Synthesis method ND1)

A solution of the compound of Example N-a-1 (3.01 g) in a mixture of methanol (40 ml) and THF (20 ml) was added with 10% palladium/carbon (410.3 mg, Merck) and one drop of concentrated hydrochloric acid, and stirred at room temperature for 5 hours under hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was added with ethyl acetate (200 ml), and washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried, and the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate Int. n-7, 2.58 g).

Synthesis of methyl 3-[3-nitro-4-(piperazin-1-yl)phenyl]acrylate (Intermediate Int. n-19) (Synthesis method NJ)

A solution of methoxycarbonylmethyl(triphenyl)phosphonium bromide (1.1 g, TCI) in THF (12.5 ml) was added with sodium hydride (115 mg, WAKO) under ice cooling, warmed to room temperature, then added dropwise with a solution of 3-nitro-4-(piperazin-1-yl)benzaldehyde (550.6 mg, MAYB) in THF (12.5 ml), and stirred at the same temperature for 16.5 hours. The reaction mixture was poured into brine (40 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (Intermediate Int. n-19, 511 mg).

Synthesis of methyl 3-[3-amino-4-(piperazin-1-yl)phenyl]propionate (Intermediate Int. n-20) (Synthesis method ND1)

According to the procedure described in the synthesis method of Intermediate Int. n-7 (Synthesis method ND1) provided that the reaction was carried out in ethyl acetate for 13 hours, Intermediate Int. n-19 (505 mg) and 10% palladium/carbon (50 mg) were reacted and treated to obtain the title compound (Intermediate Int. n-20, 658.9 mg).

Synthesis of methyl 3-[3-bromo-4-(piperazin-1-yl)phenyl]propionate (Intermediate Int. n-21) (Synthesis method NI)

A solution of hydrobromic acid (570 μl) in methanol (2.3 ml) was added dropwise with a solution of Intermediate Int. n-20 (235 mg) in methanol (2.3 ml) over 10 minutes under ice cooling. This reaction mixture was added with an aqueous solution (250 μl) of sodium nitrite (69 mg, WAKO). The reaction mixture was added dropwise with an aqueous solution (2.3 ml) of copper(II) bromide (222 mg, WAKO) heated to 50° C. over 15 minutes, stirred for 4 hours at the same temperature, and then further stirred at room temperature for 12.5 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (20 ml), and extracted with ethyl acetate (40 ml). The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-21, 89 mg).

Synthesis of methyl 4-fluoro-3-bromocinnamate (Intermediate Int. n-25) (Synthesis method NL)

According to the procedure described in the synthesis method of Intermediate Int. n-1 (Synthesis method NL) provided that the reaction was carried out for 1 hour, 3-bromo-4-fluorocinnamic acid (3.30 g, LANC) and thionyl chloride (1.5 ml) were reacted and treated to obtain the title compound (Intermediate Int. n-25, 3.47 g)

Synthesis of methyl 3-[3-bromo-4-(piperidin-1-yl)phenyl]cinnamate (Intermediate Int. n-26) (Synthesis method NG)

A solution of Intermediate Int. n-25 (136.4 mg) in DMSO (5 ml) was added with potassium carbonate (109.8 mg) and piperidine (84.8 μl, TCI), and stirred at 90° C. for 15 hours. The reaction mixture was extracted with ethyl acetate (50 ml), and then the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:isopropyl ether=6:1) to obtain the title compound (Intermediate Int. n-26, 120.4 mg).

Synthesis of methyl 3-[3-bromo-4-(piperidin-1-yl)phenyl]propionate (Intermediate Int. n-27) (Synthesis method ND2)

According to a procedure described in literature [D. J. Hart et al., Journal of Organic Chemistry (J. Org. Chem.), 1987, vol. 52, p. 4665], a solution of Intermediate Int. n-26 (690.6 mg) in dimethoxyethane (100 ml) was added with p-toluenesulfonhydrazide (2.97 g, TCI), and refluxed by heating at 110° C. Then, the reaction mixture was added dropwise with an aqueous solution (100 ml) of sodium acetate (2.85 g, WAKO) over 2 hours, and further stirred for 1 hour. The reaction mixture was extracted with dichloromethane (450 ml), and the organic layer was washed with water, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Intermediate Int. n-27, 648.2 mg).

Synthesis of 3-bromo-(4-imidazol-1-yl)benzaldehyde (Intermediate Int. n-32) (Synthesis method NG)

According to the procedure described in the synthesis method of Intermediate Int. n-26 (Synthesis method NG) provided that the reaction was performed for 20 hours, and the column chromatography was performed with chloroform:methanol=100:1, 3-bromo-4-fluorobenzaldehyde (1.246 g, TCI), potassium carbonate (825.1 mg) and imidazole (444 mg, TCI) were reacted and treated to obtain the title compound (Intermediate Int. n-32, 986.1 mg).

Synthesis of ethyl 3-[3-bromo-(4-imidazol-1-yl)phenyl]acrylate (Intermediate Int. n-33) (Synthesis method NJ)

A solution of Intermediate Int. n-32 (986.1 mg) and ethyl diethylphosphonoacetate (705 μl) in 1,2-dimethoxyethane (8 ml) was added with 60% sodium hydride (180.2 mg) under ice cooling, stirred for 10 minutes, then warmed to room temperature, and stirred for 1 hour. The reaction mixture was added with dichloromethane (60 ml) for extraction, and the organic layer was washed with saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, dichloromethane:methanol=100:1) to obtain the title compound (Intermediate Int. n-33, 1.00 g).

Synthesis of methyl 3-(4-cyclopentylaminophenyl)propionate (Intermediate Int. n-38) (Synthesis method NC1)

According to the procedure described in the synthesis method of Intermediate Int. n-3 provided that the reaction was carried out for 6 hours, Intermediate Int. n-1 (1.03 g), cyclopentanone (450 μl, TCI), sodium triacetoxyborohydride (1.56 g) and acetic acid (350 μl) were reacted and treated to obtain the title compound (Intermediate Int. n-37, 1.21 g).

Synthesis of methyl 3-(4-cyclopentylamino-3,5-dibromophenyl)propionate (Intermediate Int. n-39) (Synthesis method NK)

A solution of Intermediate Int. n-37 (1.21 g) in acetonitrile was warmed to 35° C., then added with N-bromosuccinimide (2.44 g, TCI), and stirred for 1 hour. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (150 ml), washed successively with aqueous sodium thiosulfate, saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Intermediate Int. n-38, 1.41 g).

Synthesis of 2-bromopyridine-5-carbaldehyde (Intermediate Int. n-44) (Synthesis method NM)

According to a procedure described in literature (Xin Wang et al., Tetrahedron. Lett., 2000, vol. 41, p. 4335], a solution of 2,5-dibromopyridine (3.17 g) in anhydrous diethyl ether (140 ml) was added dropwise with a 1.6 M solution of n-butyl lithium in hexane (11 ml) with cooling at −78° C. under argon gas atmosphere over 5 minutes, and stirred for 20 minutes. This reaction mixture was added dropwise with dehydrated DMF (1 ml) over 3 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was added with water (20 ml), and extracted with ethyl acetate (30 ml×2). The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Intermediate Int. n-44, 1.46 g).

Synthesis of ethyl 3-(2-bromopyridin-5-yl)acrylate (Intermediate Int. n-45) (Synthesis method NJ)

According to the procedure described in the synthesis method of Intermediate n-7 provided that the reaction was carried out for 15 minutes, Intermediate Int. n-44 (1.45 g), ethyl diethylphosphonoacetate (2.1 ml) and 60% sodium hydride (355 mg) were reacted and treated to obtain the title compound (Intermediate Int. n-45, 1.87 g).

Synthesis of ethyl 3-[2-(piperidin-1-yl)pyridin-5-yl]acrylate (Intermediate Int. n-46) (Synthesis method NG)

Intermediate Int. n-45 (565.7 mg) was added with potassium carbonate (286.4 mg) and piperidine (3 ml), and stirred at 90° C. for 21 hours. The reaction mixture was added with ethyl acetate (50 ml), washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-46, 165.9 mg).

Synthesis of ethyl 3-[2-(piperidin-1-yl)pyridin-5-yl]propionate (Intermediate Int. n-47) (Synthesis method ND1)

According to the procedure described in the synthesis method of Intermediate Int. n-7 with the modifications that the reaction was carried out for 1 hour, and the purification was performed by column chromatography (Quad, hexane:ethyl acetate 6:1), Intermediate Int. n-46 (392 mg) and 10% palladium/carbon (30 mg) were reacted and treated to obtain the title compound (Intermediate Int. n-47; 246 mg).

Synthesis of ethyl 3-[3-bromo-2-(piperidin-1-yl)pyridin-3-yl]propionate (Intermediate Int. n-48) (Synthesis method NK2)

A solution of Intermediate Int. n-47 (242 mg) in acetonitrile was added with bromine (84 μl), and stirred at 40° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (50 ml), washed successively with aqueous sodium thiosulfate, saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Intermediate Int. n-48, 224 mg).

Synthesis of 2-benzylaminopyridine-5-carbaldehyde (Intermediate Int. n-59) (Synthesis Method NG)

Intermediate Int. n-44 (102.0 mg) was added with benzylamine (1 ml, TCI), and stirred at 120° C. for 39 hours. The reaction mixture was added with ethyl acetate (50 ml), washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-59, 58.3 mg).

Synthesis of 2-benzylamino-3-bromopyridine-5-carbaldehyde (Intermediate Int. n-60) (Synthesis method NK)

A solution of Intermediate Int. n-59 (56.8 mg) in acetonitrile was added with N-bromosuccinimide (134 mg), and stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (50 ml), washed successively with aqueous sodium thiosulfate, saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate Int. n-60, 50 mg).

Synthesis of ethyl 3-(2-benzylamino-3-bromopyridin-5-yl)acrylate (Intermediate Int. n-61) (Synthesis method NJ)

According to the procedure described in the synthesis method of Intermediate Int. n-7 provided that the reaction was carried out for 30 minutes, Intermediate Int. n-60 (49.1 g), ethyl diethylphosphonoacetate (92 μl) and 60% sodium hydride (30 mg) were reacted and treated to obtain the title compound (Intermediate Int. n-61, 28 mg).

Synthesis of ethyl 3-(2-benzylamino-3-bromopyridin-5-yl)propionate (Intermediate Int. n-62) (Synthesis method ND2)

According to the procedure described in the synthesis method of Intermediate Int. n-27 provided that the reaction was carried out for 4 hours, Intermediate Int. n-60 (49.1 mg), p-toluenesulfonhydrazide (320.6 mg) and sodium acetate (412.4 mg) were reacted and treated to obtain the title compound (Intermediate Int. n-62, 38.9 mg).

Synthesis of methyl 3-(4-amino-3-bromo-5-nitrophenyl)propionate (Intermediate Int. n-76) (Synthesis method NM)

A solution obtained by adding potassium nitrate (1.10 g) to a solution of Intermediate Int. n-2 (2.57 g) in acetic anhydride (20 ml) under ice cooling and stirring them for 10 minutes was added dropwise with concentrated sulfuric acid (700 μl) over 10 minutes. The reaction mixture was stirred for 10 minutes at the same temperature, then warmed to room temperature, and further stirred for 30 minutes. The reaction mixture was poured into 1 N aqueous sodium hydroxide (250 ml) containing ice, and extracted with isopropyl ether (200 ml×2). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=3:1) to obtain the title compound (Intermediate Int. n-76, 0.72 g).

Typical examples of the intermediates for synthesizing the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-Int. N-1 to Table-Int. N-8. In the tables, the intermediate numbers “Int. n-(number)” are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”. Further, the compounds indicated as “Single” in the columns of “Single or Double” in the tables are compound in which two of the carbon atoms binding the benzene ring and carbonyl group in the compounds are bound with a single bond, and those indicated as “Double” in the same are compounds in which two of the carbon atoms binding the benzene ring and carbonyl group in the compounds are bound with a double bond. The aldehydes and ketones used for the synthesis of the compounds are mentioned in Table-Carb, and amines used for the same are mentioned in Table-AMN.

TABLE Carb Reagent Aldehyde or Ketone Manufacture CHO1 HCHO WAKO CHO2 CH₃CHO Aldlich CHO3 CH₃CH₂CHO TCI CHO4 nPrCHO TCI CHO5 Acetone WAKO CHO6 nBuCHO TCI CHO7 iPrCHO TCI CHO8 BnCHO TCI CHO9 4FBnCHO TCI CHO10 2FBnCHO TCI CHO11 3FBnCHO TCI CHO12 2ClBnCHO TCI CHO13 2BrBnCHO TCI CHO14 2,3DFBnCHO TCI CHO15 3,4DFBnCHO TCI CHO16 4PhBnCHO TCI CHO17 2CF₃BnCHO TCI CHO18 2,3DClBnCHO TCI CHO19 2-ThiofeneCHO(2-TFCHO) TCI CHO20 3-ThiofeneCHO(3-TFCHO) TCI CHO21 2-FuranCHO(2-FRCHO) TCI CHO22 Cyclopentanone TCI CHO23 Cyclohexanone TCI CHO24 2(Me)cHexanone TCI CHO25 2-Indanone Aldlich

TABLE AMN Reagent Amine Manufacture AMN1

TCI AMN2

TCI AMN3

TCI AMN4

TCI AMN5

TCI AMN6

TCI AMN7

TCI AMN8 EtMeNH Aldrich AMN9 Et₂NH Aldrich AMN10 nPrMeNH Aldrich AMN11 iPrMeNH Aldrich AMN12 nBuMeNH Aldrich AMN13 nBuEtNH Aldrich AMN14 iBuMeNH Aldrich AMN15 4MeBnNH₂ Aldrich AMN16 3MeBnNH₂ Aldrich AMN17 2MeBnNH₂ Aldrich AMN18 4FBnNH₂ Aldrich AMN19 3FBnNH₂ Aldrich AMN20 2FBnNH₂ Aldrich AMN21 3MeOBnNH₂ Aldrich AMN22 4MeOBnNH₂ Aldrich AMN23 2MeOBnNH₂ Aldrich AMN24 4CF₃BnNH₂ Aldrich AMN25 2EtOBnNH₂ Aldrich AMN26 3iPrOBnNH₂ Sigma-Aldrich AMN27 3,5DFBnNH₂ Aldrich

TABLE Int.N-1

LCMS Exp. Syn SM1 SM2 Rz method RTime Mass Int.n-5 NC2 Int.n-2 CHO10 2FBn C 366 (M⁺) Int.n-6 NC1 Int.n-2 CHO11 3FBn C 366 (M⁺) Int.n-12 NC2 Int.n-2 CHO2 Et C 386 (M⁺) Int.n-13 NC2 Int.n-2 CHO3 nPr D 5.02 300 (M⁺) Int.n-14 NC2 Int.n-2 CHO5 iPr D 5.38 341 (M⁺) Int.n-15 NC2 Int.n-2 CHO7 iBu D 5.50 400 (M⁺) Int.n-16 NC2 Int.n-2 CHO22 cPen C 326 (M⁺) Int.n-17 NC2 Int.n-2 CHO23 cHex C 340 (M⁺) Int.n-18 NC2 Int.n-2 CHO24 2(Me)cHex C 354 (M⁺)

TABLE Int.N-2

LCMS me- Exp. Syn SM1 AR thod RTime Mass Int.n-8 ND1 N-a-3 5-Ind C 295 (M⁺ + 1) Int.n-9 ND1 N-a-5 1Me-5-Ind C 309 (M⁺ + 1) Int.n-10 ND1 N-a-7 5-1Idz C 296 (M⁺ + 1) Int.n-11 ND1 N-a-9 1Me-5-1HIdz C 310 (M⁺ + 1)

TABLE Int.N-3

Single or LCMS Exp. Syn. Rs G Double method RTime Mass Int.n-22 NJ

NO2 Double A 3.91 293 (M⁺ + 1) Int.n-23 ND1

NH2 Single A 2.97 265 (M⁺ + 1) Int.n-24 NI

Br Single A 4.31 328 (M⁺)

TABLE Int.N-4

Single or LCMS Exp. Syn SM1 RzRyN Double method RTime Mass Int.n-28 NC2 Int.n-25

Double A 6.54 338 (M⁺) Int.n-29 NC1 Int.n-28

Single A 6.01 342 (M⁺ + 1) Int.n-30 NC2 Int.n-25

Double A 6.29 340 (M⁺ + 1) Int.n-31 NC1 Int.n-30

Single A 6.12 342 (M⁺ + 1) Int.n-33 NC2 Int.n-32

Double C 307 (M⁺) Int.n-35 NC2 Int.n-32

Double C 306 (M⁺) Int.n-36 NC2 Int.n-25

Double A 5.60 310 (M⁺) Int.n-37 NC2 Int.n-32

Double C 326 (M⁺)

TABLE Int.N-5

LCMS Exp. Syn SM1 RzRyN method RTime Mass Int.n-32 NC2 Int.n-25

C 351 (M⁺) Int.n-34 NC2 Int.n-25

C 250 (M⁺)

TABLE Int.N-6

LCMS Exp. Syn SM1 SM2 Rz Z′ H or Br method RTime Mass Int.n-40 NC1 Int.n-1 CHO3 nPr H H C 222 (M⁺ + 1) Int.n-41 NK Int.n-40 nPr Br Br C 380 (M⁺ + 1) Int.n-42 NC1 Int.n-1 CHO5 iPr H H C 222 (M⁺ + 1) Int.n-43 NK Int.n-42 iPr Br Br C 380 (M⁺ + 1)

TABLE Int.N-7

LCMS Exp. Syn RzRyN method RTime Mass Int.n-48 NG cHex C 327 (M⁺) Int.n-49 NG cPen C 313 (M⁺) Int.n-50 NG 4(Me)cHex C 341 (M⁺) Int.n-51 NG

C 343 (M⁺) Int.n-52 NG cHep C 355 (M⁺) LCMS Exp. Syn Rz Ry method RTime Mass Int.n-53 NG Et Me C 301 (M⁺) Int.n-54 NG Et Et C 315 (M⁺) Int.n-55 NG nPr Me C 315 (M⁺) Int.n-56 NG iPr Me C 315 (M⁺) Int.n-57 NG nBu Me C 329 (M⁺) Int.n-58 NG iBu Me C 329 (M⁺) Int.n-63 NG 4MeBn H C 363 (M⁺) Int.n-64 NG 3MeBn H C 363 (M⁺) Int.n-65 NG 2MeBn H C 363 (M⁺) Int.n-66 NG 4FBn H C 368 (M⁺ + 1) Int.n-67 NG 3FBn H C 368 (M⁺ + 1) Int.n-68 NG 2FBn H C 368 (M⁺ + 1) Int.n-69 NG 4MeOPh H C 365 (M⁺) Int.n-70 NG 3MeOPh H C 365 (M⁺) Int.n-71 NG 2MeOPh H C 365 (M⁺) Int.n-72 NG 4CF3Ph H C 403 (M⁺) Int.n-73 NG 2EtOPh H C 380 (M⁺ + 1) Int.n-74 NG 3iPrOPh H C 393 (M⁺) Int.n-75 NG 3,5DFPh H C 372 (M⁺ + 1)

TABLE Int.N-8

LCMS Exp. Syn SM1 SM2 Rz Ry method RTime Mass Int.n-77 NC2 Int.n-76 CHO22 cPen H C 371 (M⁺) Int.n-78 NC2 Int.n-76 CHO3 nPr H C 345 (M⁺) Int.n-79 NC2 Int.n-76 CHO5 iPr H C 345 (M⁺) Int.n-80 NC2 Int.n-76 CHO25 2-Indane H C 419 (M⁺) Int.n-81 NC2 Int.n-76 CHO23 cHex H C 385 (M⁺) Int.n-82 NC2 Int.n-76 CHO24 2(Me)cHex H C 399 (M⁺) Int.n-83 NC1 Int.n-77 CHO1 cPen Me C 385 (M⁺) Int.n-84 NC1 Int.n-78 CHO1 nPr Me C 359 (M⁺) Int.n-85 NC1 Int.n-79 CHO1 iPr Me C 359 (M⁺) Int.n-86 NC1 Int.n-80 CHO1 2-Indane Me C 433 (M⁺) Int.n-87 NC1 Int.n-81 CHO1 cHex Me C 399 (M⁺) Int.n-88 NC1 Int.n-82 CHO1 2(Me)cHex Me C 413 (M⁺) Int.n-89 NC1 Int.n-76 CHO8 Bn H C 393 (M⁺) Int.n-90 NC1 Int.n-76 CHO9 4FBn H C 411 (M⁺) Int.n-91 NC2 Int.n-76 CHO10 2FBn H C 411 (M⁺) Int.n-92 NC2 Int.n-76 CHO11 3FBn H C 411 (M⁺) Int.n-93 NC2 Int.n-76 CHO14 2,3DFBn H C 429 (M⁺) Int.n-94 NC2 Int.n-76 CHO15 3,4DFBn H C 429 (M⁺) Int.n-95 NC2 Int.n-76 CHO16 4PhBn H C 469 (M⁺) Int.n-96 NC2 Int.n-76 CHO17 2CF3Bn H C 461 (M⁺) Int.n-97 NC2 Int.n-76 CHO19 2-TF H C 399 (M⁺) Int.n-98 NC2 Int.n-76 CHO20 3-TF H C 399 (M⁺) Int.n-99 NC2 Int.n-76 CHO21 2-FR H C 383 (M⁺) Int.n-100 NC1 Int.n-89 CHO1 Bn Me C 407 (M⁺) Int.n-101 NC1 Int.n-90 CHO1 4FBn Me C 428 (M⁺) Int.n-102 NC1 Int.n-91 CHO1 2FBn Me C 425 (M⁺) Int.n-103 NC1 Int.n-92 CHO1 3FBn Me C 425 (M⁺) Int.n-104 NC1 Int.n-93 CHO1 2,3DFBn Me C 443 (M⁺) Int.n-105 NC1 Int.n-94 CHO1 3,4DFBn Me C 443 (M⁺) Int.n-106 NC1 Int.n-95 CHO1 4PhBn Me C 483 (M⁺) Int.n-107 NC1 Int.n-96 CHO1 2CF3Bn Me C 475 (M⁺) Int.n-108 NC1 Int.n-97 CHO1 2-TF Me C 413 (M⁺) Int.n-109 NC1 Int.n-98 CHO1 3-TF Me C 413 (M⁺) Int.n-110 NC1 Int.n-99 CHO1 2-FR Me C 397 (M⁺) LCMS Exp. Syn SM1 SM2 RzRyN method RTime Mass Int.n-111 NM Int.n-21

C 357 (M⁺) Int.n-112 NM Int.n-24

C 373(M⁺) Int.n-113 NM Int.n-27

C 371(M⁺) Int.n-114 NM Int.n-29

C 385 (M⁺) Int.n-115 NM Int.n-31

C 385 (M⁺)

Example N-a-1 Synthesis of methyl 3-[4-benzylamino-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-a-1) (Synthesis method NB1)

A solution of Intermediate n-3 (8.18 g) in toluene (60 ml) was added with 2-naphthaleneboronic acid (5.04 g, TCI), 2 M aqueous sodium carbonate (21.6 ml), methanol (24 ml) and tetrakistriphenylphosphine palladium(0) (henceforth abbreviated as “(Ph₃P)₄Pd”, 1.94 g, Nacalai Tesque), and stirred at 90° C. for 15 hours. The reaction mixture was added with ethyl acetate (300 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (Compound No. N-a-1, 5.70 g).

Example N-a-2 Synthesis of 3-[4-benzylamino-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. N-a-2) (Synthesis method NA)

A solution of the compound of Example N-a-1 (51 mg) in methanol (5.0 ml) was added with 2 N aqueous sodium hydroxide (130 μl), and stirred at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, then neutralized with 5% aqueous hydrochloric acid under ice cooling, and then extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. N-a-2, 47 mg).

Example N-a-251 Synthesis of methyl 3-[4-(N-benzyl-N-methylamino)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-a-25) (Synthesis method NC1)

According to the procedure described in the synthesis method of Intermediate n-3 provided that the reaction was carried out for 5 hours, the compound of Example N-a-1 (234.2 mg), 30% aqueous solution of formaldehyde (208.8 μl, WAKO) and sodium cyanotrihydroridoborate (140.9 mg) were reacted and treated to obtain the title compound (Compound No. N-a-25, 176.3 mg).

Example N-A-137 Synthesis of methyl 3-{3-(1-methyl-1H-indol-5-yl)-4-[N-(1-phenylethyl)amino]phenyl}propionate (Compound No. N-a-137) (Synthesis method NE1)

According to a procedure described in literature [Shin-Shyong Tseng et al., Journal of Organic Chemistry (J. Org. Chem.), 1979, vol. 44, p. 4113], a solution of Intermediate n-9 (630.7 mg) in methylene chloride (10 ml) was added with triethylamine (405 μl, Kokusan Chemical), cooled to −78° C., then added dropwise with trifluoromethanesulfonyl chloride (426 μl, TCI), and stirred for 1.5 hours. The reaction mixture was poured into ice water (10 ml), and added with dichloromethane (30 ml) for extraction. The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain a crude product. A solution of the obtained crude product in DMF (15 ml) was added with potassium carbonate (394.2 mg) and (1-bromoethyl)benzene (386.4 μl, TCI), and stirred at room temperature for 13 hours. The reaction mixture was extracted with ethyl acetate (100 ml), and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. N-a-137, 310.3 mg).

Example N-a-141 Synthesis of methyl 3-[3-(1-methyl-1H-indol-5-yl)-4-{N-[2-(4-fluorophenyl)ethyl]amino}phenyl]propionate (Compound No. N-a-141) (Synthesis method NE2)

A solution of Intermediate n-9 (210.1 mg) in methylene chloride (10 ml) was added with triethylamine (135 μl, Kokusan Chemical), cooled to −78° C., then added dropwise with trifluoromethanesulfonyl chloride (143 μl, TCI), and stirred for 1.5 hours. The reaction mixture was poured into ice water (10 ml), and added with dichloromethane (15 ml) for extraction. The organic layer was washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain a crude product. A solution of the obtained crude product in anhydrous DMF (15 ml) was added with triphenylphosphine (485.9 g, WAKO), di-t-butyl azodicarboxylate (299.8 mg, Ald) and 4-fluorophenylethyl alcohol (357 μl, TCI), and stirred at room temperature for 12 hours. The reaction mixture was added with water (10 ml) and ethyl acetate (10 ml) for extraction, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. N-a-141, 63.5 mg).

Example N-a-143 Synthesis of methyl 3-[4-(N-acetyl-N-benzylamino)-3-(1-methyl-1H-indol-5-yl)phenyl]propionate (Compound No. N-a-143) (Synthesis method NF)

A solution of Compound No. N-a-5 (32 mg) in methylene chloride (3 ml) was added with pyridine (49.6 μl, TCI) and acetyl chloride (50 μl, TCI), and stirred for 13 hours. The reaction mixture was added with water (1 ml), and the solvent was evaporated. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. N-a-143, 20.3 mg).

Example N-a-153 Synthesis of methyl 3-[4-benzoylamino-3-(1-methyl-1H-indol-5-yl)phenyl]propionate (Compound No. N-a-153) (Synthesis method NF)

According to the procedure described in the synthesis method of the compound of Example N-a-143 provided that the reaction was carried out for 16 hours, Intermediate Int. n-9 (26.5 mg), pyridine (23.8 μl) and benzoyl chloride (30 μl, WAKO) were reacted and treated to obtain the title compound (Compound No. N-a-153, 18.4 mg).

Examples N-a-1 to N-a-166

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-A-1 to Table-N-A-4. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-A-1

LCMS Exp. Syn SM1 SM2 Rz Ry Y Zx AR method RTime Mass N-a-1 NB1 Int.n-3 BRN1 Bn H Me H 2-Nap C 396 (M⁺ + 1) N-a-2 NA N-a-1 Bn H H H 2-Nap C 382 (M⁺ + 1) N-a-3 NB1 Int.n-3 BRN2 Bn H Me H 5-1Ind C 385 (M⁺ + 1) N-a-4 NA N-a-3 Bn H H H 5-1Ind C 371 (M⁺ + 1) N-a-5 NB1 Int.n-3 BRN3 Bn H Me H 1Me-5-Ind C 399 (M⁺ + 1) N-a-6 NA N-a-5 Bn H H H 1Me-5-Ind C 385 (M⁺ + 1) N-a-7 NB1 Int.n-3 BRN4 Bn H Me H 1Et-5-Ind C 413 (M⁺ + 1) N-a-8 NA N-a-1 Bn H H H 1Et-5-Ind C 399 (M⁺ + 1) N-a-9 NB1 Int.n-3 BRN5 Bn H Me H 5-1HIdz C 386 (M⁺ + 1) N-a-10 NA N-a-9 Bn H H H 5-1HIdz C 372 (M⁺ + 1) N-a-11 NB1 Int.n-3 BRN6 Bn H Me H 1Me-5- C 400 (M⁺ + 1) 1HIdz N-a-12 NA N-a-11 Bn H H H 1Me-5- C 386 (M⁺ + 1) 1HIdz N-a-13 NB1 Int.n-3 BRN7 Bn H Me H 1Et-5- C 414 (M⁺ + 1) 1HIdz N-a-14 NA N-a-13 Bn H H H 1Et-5- C 400 (M⁺ + 1) 1HIdz N-a-15 NB1 Int.n-3 BRN8 Bn H Me H 2Me-5- C 400 (M⁺ + 1) 2HIdz N-a-16 NA N-a-15 Bn H H H 2Me-5- C 386 (M⁺ + 1) 2HIdz N-a-17 NB1 Int.n-3 BRN9 Bn H Me H 5-Bzt C 403 (M⁺ + 1) N-a-18 NA N-a-17 Bn H H H 5-Bzt C 389 (M⁺ + 1) N-a-19 NB1 Int.n-3 BRN10 Bn H Me H 3-Qu C 397 (M⁺ + 1) N-a-20 NA N-a-19 Bn H H H 3-Qu C 383 (M⁺ + 1) N-a-21 NB1 Int.n-3 BRN11 Bn H Me H 6-Qu C 397 (M⁺ + 1) N-a-22 NA N-a-21 Bn H H H 6-Qu C 383 (M⁺ + 1) N-a-23 NB1 Int.n-3 BRN12 Bn H Me H 6-IQ C 397 (M⁺ + 1) N-a-24 NA N-a-23 Bn H H H 6-IQ C 383 (M⁺ + 1) N-a-25 NC1 N-a-1 CHO1 Bn Me Me H 2-Nap C 410 (M⁺ + 1) N-a-26 NA N-a-25 Bn Me H H 2-Nap C 396 (M⁺ + 1) N-a-27 NC1 N-a-1 CHO2 Bn Et Me H 2-Nap C 424 (M⁺ + 1) N-a-28 NA N-a-27 Bn Et H H 2-Nap C 410 (M⁺ + 1) N-a-29 NC1 N-a-3 CHO1 Bn Me Me H 5-1Ind C 399 (M⁺ + 1) N-a-30 NA N-a-29 Bn Me H H 5-1Ind C 384 (M⁺ + 1) N-a-31 NC1 N-a-5 CHO1 Bn Me Me H 1Me-5-Ind C 413 (M⁺ + 1) N-a-32 NA N-a-31 Bn Me H H 1Me-5-Ind C 399 (M⁺ + 1) N-a-33 NB1 Int.n-4 BRA1 4FBn H Me H 2-Nap C 414 (M⁺ + 1) N-a-34 NA N-a-33 4FBn H H H 2-Nap C 400 (M⁺ + 1) N-a-35 NB1 Int.n-4 BRA2 4FBn H Me H 5-1Ind D 5.20 403 (M⁺ + 1) N-a-36 NA N-a-35 4FBn H H H 5-1Ind D 4.73 389 (M⁺ + 1) N-a-37 NB1 Int.n-4 BRA3 4FBn H Me H 1Me-5-Ind D 5.51 417 (M⁺ + 1) N-a-38 NA N-a-37 4FBn H H H 1Me-5-Ind D 4.78 403 (M⁺ + 1) N-a-39 NB1 Int.n-4 BRA5 4FBn H Me H 5-1HIdz D 4.60 404 (M⁺ + 1) N-a-40 NA N-a-39 4FBn H H H 5-1HIdz C 390 (M⁺ + 1) N-a-41 NB1 Int.n-4 BRA6 4FBn H Me H 1Me-5- A 4.85 418 (M⁺ + 1) 1HIdz N-a-42 NA N-a-41 4FBn H H H 1Me-5- A 4.14 404 (M⁺ + 1) 1HIdz N-a-43 NB1 Int.n-4 BRA10 4FBn H Me H 3-Qu D 4.72 415 (M⁺ + 1) N-a-44 NA N-a-43 4FBn H H H 3-Qu C 401 (M⁺ + 1) N-a-45 NC2 N-a-35 CHO1 4FBn Me Me H 5-Ind D 4.17 417 (M⁺ + 1) N-a-46 NA N-a-45 4FBn Me H H 5-Ind D 3.38 403 (M⁺ + 1) N-a-47 NC2 N-a-37 CHO1 4FBn Me Me H 1Me-5-Ind C 431 (M⁺ + 1) N-a-48 NA N-a-47 4FBn Me H H 1Me-5-Ind C 418 (M⁺ + 1) N-a-49 NC2 N-a-41 CHO1 4FBn Me Me H 1Me-5- C 432 (M⁺ + 1) 1HIdz N-a-50 NA N-a-49 4FBn Me H H 1Me-5- C 418 (M⁺ + 1) 1HIdz N-a-51 NC2 N-a-37 CHO2 4FBn Et Me H 1Me-5-Ind C 445 (M⁺ + 1) N-a-52 NA N-a-51 4FBn Et H H 1Me-5-Ind C 431 (M⁺ + 1) N-a-53 NC2 N-a-39 CHO2 4FBn Et Me H 5-1Idz C 433 (M⁺ + 1) N-a-54 NA N-a-53 4FBn Et H H 5-1Idz C 419 (M⁺ + 1) N-a-55 NB1 Int.n-5 2FBn H Me H 2-Nap C 414 (M⁺ + 1) N-a-56 NA N-a-55 2FBn H H H 2-Nap C 400 (M⁺ + 1) N-a-57 NB1 Int.n-5 2FBn H Me H 1Me-5-Ind C 417 (M⁺ + 1) N-a-58 NA N-a-57 2FBn H H H 1Me-5-Ind C 403 (M⁺ + 1) N-a-59 NB1 Int.n-5 2FBn H Me H 1Me-5- C 418 (M⁺ + 1) 1HIdz N-a-60 NA N-a-59 2FBn H H H 1Me-5- C 404 (M⁺ + 1) 1HIdz N-a-61 NC2 N-a-59 CHO1 2FBn Me Me H 1Me-5- C 432 (M⁺ + 1) 1HIdz N-a-62 NA N-a-61 2FBn Me H H 1Me-5- C 418 (M⁺ + 1) 1HIdz N-a-63 NB1 Int.n-6 3FBn H Me H 2-Nap C 414 (M⁺ + 1) N-a-64 NA N-a-63 3FBn H H H 2-Nap C 400 (M⁺ + 1) N-a-65 NB1 Int.n-6 3FBn H Me H 5-1Ind C 403 (M⁺ + 1) N-a-66 NA N-a-65 3FBn H H H 5-1Ind C 389 (M⁺ + 1) N-a-67 NB1 Int.n-6 3FBn H Me H 1Me-5-Ind C 417 (M⁺ + 1) N-a-68 NA N-a-67 3FBn H H H 1Me-5-Ind C 403 (M⁺ + 1) N-a-69 NC2 N-a-67 CHO1 3FBn Me Me H 1Me-5-Ind C 431 (M⁺ + 1) N-a-70 NA N-a-69 3FBn Me H H 1Me-5-Ind C 417 (M⁺ + 1) N-a-71 NC1 Int.n-7 CHO12 2ClBn H Me H 2-Nap C 430 (M⁺ + 1) N-a-72 NA N-a-7 2ClBn H H H 2-Nap C 416 (M⁺ + 1) N-a-73 NC1 Int.n-7 CHO13 2BrBn H Me H 2-Nap C 475 (M⁺ + 1) N-a-74 NA N-a-73 2BrBn H H H 2-Nap C 461 (M⁺ + 1) N-a-75 NC1 Int.n-7 CHO14 2,3DFBn H Me H 2-Nap C 432 (M⁺ + 1) N-a-76 NA N-a-75 2,3DFBn H H H 2-Nap C 418 (M⁺ + 1) N-a-77 NC1 Int.n-7 CHO21 2-FR H Me H 2-Nap C 386 (M⁺ + 1) N-a-78 NA N-a-77 2-FR H H H 2-Nap C 372 (M⁺ + 1) N-a-79 NC1 Int.n-7 CHO20 3-TF H Me H 2-Nap C 402 (M⁺ + 1) N-a-80 NA N-a-79 3-TF H H H 2-Nap C 388 (M⁺ + 1) N-a-81 NC1 Int.n-7 CHO17 2CF3Bn H Me H 2-Nap C 464 (M⁺ + 1) N-a-82 NA N-a-80 2CF3Bn H H H 2-Nap C 450 (M⁺ + 1) N-a-83 NC1 Int.n-8 CHO12 2ClBn H Me H 5-1Ind C 302 (M⁺ + 1) N-a-84 NA N-a-80 2ClBn H H H 5-1Ind C 288 (M⁺ + 1) N-a-85 NC2 N-a-80 CHO1 2ClBn Me Me H 5-1Ind C 316 (M⁺ + 1) N-a-86 NA N-a-85 2ClBn Me H H 5-1Ind C 302 (M⁺ + 1) N-a-87 NC1 Int.n-8 CHO14 2,3DFBn H Me H 5-1Ind C 304 (M⁺ + 1) N-a-88 NA N-a-87 2,3DFBn H H H 5-1Ind C 290 (M⁺ + 1) N-a-89 NC1 Int.n-8 CHO16 4PhBn H Me H 5-1Ind C 344 (M⁺ + 1) N-a-90 NA N-a-89 4PhBn H H H 5-1Ind C 330 (M⁺ + 1) N-a-91 NC1 Int.n-8 CHO19 2-TF H Me H 5-Ind C 391 (M⁺ + 1) N-a-92 NA N-a-91 2-TF H H H 5-Ind C 377 (M⁺ + 1) N-a-93 NC1 Int.n-8 CHO17 2CF3Bn H Me H 5-Ind C 453 (M⁺ + 1) N-a-94 NA N-a-93 2CF3Bn H H H 5-Ind C 439 (M⁺ + 1) N-a-95 NC1 Int.n-8 CHO18 2,3DClBn H Me H 5-Ind C 454 (M⁺ + 1) N-a-96 NA N-a-71 2,3DClBn H H H 5-Ind C 440 (M⁺ + 1) N-a-97 NC1 Int.n-9 CHO13 2BrBn H Me H 1Me-5-Ind C 478 (M⁺ + 1) N-a-98 NA N-a-97 2BrBn H H H 1Me-5-Ind C 464 (M⁺ + 1) N-a-99 NC1 Int.n-9 CHO15 3,4DFBn H Me H 1Me-5-Ind C 435 (M⁺ + 1) N-a-100 NA N-a-99 3,4DFBn H H H 1Me-5-Ind C 421 (M⁺ + 1) N-a-101 NC1 Int.n-9 CHO16 4PhBn H Me H 1Me-5-Ind C 475 (M⁺ + 1) N-a-102 NA N-a-101 4PhBn H H H 1Me-5-Ind C 461 (M⁺ + 1) N-a-103 NC1 Int.n-9 CHO21 2-FR H Me H 1Me-5-Ind C 389 (M⁺ + 1) N-a-104 NA N-a-103 2-FR H H H 1Me-5-Ind C 375 (M⁺ + 1) N-a-105 NC1 Int.n-9 CHO20 3-TF H Me H 1Me-5-Ind C 405 (M⁺ + 1) N-a-106 NA N-a-105 3-TF H H H 1Me-5-Ind C 391 (M⁺ + 1) N-a-107 NC1 Int.n-9 CHO18 2,3DClBn H Me H 1Me-5-Ind C 468 (M⁺ + i) N-a-108 NA N-a-107 2,3DClBn H H H 1Me-5-Ind C 454 (M⁺ + 1) N-a-109 NC1 Int.n-10 CHO13 2BrBn H Me H 5-1HIdz C 465 (M⁺ + 1) N-a-110 NA N-a-109 2BrBn H H H 5-1HIdz C 451 (M⁺ + 1) N-a-111 NC1 Int.n-10 CHO15 3,4DFBn H Me H 5-1HIdz C 422 (M⁺ + 1) N-a-112 NA N-a-111 3,4DFBn H H H 5-1HIdz C 408 (M⁺ + 1) N-a-113 NC2 N-a-111 CHO1 3,4DFBn Me Me H 5-1HIdz C 436 (M⁺ + 1) N-a-114 NA N-a-113 3,4DFBn Me H H 5-1HIdz C 422 (M⁺ + 1) N-a-115 NC1 Int.n-10 CHO21 2-FR H Me H 5-1HIdz C 376 (M⁺ + 1) N-a-116 NA N-a-115 2-FR H H H 5-1HIdz C 362 (M⁺ + 1) N-a-117 NC1 Int.n-10 CHO20 3-TF H Me H 5-1HIdz C 392 (M⁺ + 1) N-a-118 NA N-a-116 3-TF H H H 5-1HIdz C 378 (M⁺ + 1) N-a-119 NC1 Int.n-10 CHO17 2CF3Bn H Me H 5-1HIdz C 454 (M⁺ + 1) N-a-120 NA N-a-120 2CF3Bn H H H 5-1HIdz C 440 (M⁺ + 1) N-a-121 NC1 Int.n-10 CHO18 2,3DClBn H Me H 1Me-5- C 469 (M⁺ + 1) 1HIdz N-a-122 NA N-a-122 2,3DClBn H H H 1Me-5- C 455 (M⁺ + 1) 1HIdz N-a-123 NC1 Int.n-11 CHO12 2ClBn H Me H 1Me-5- C 434 (M⁺ + 1) 1HIdz N-a-124 NA N-a-123 2ClBn H H H 1Me-5- C 420 (M⁺ + 1) 1HIdz N-a-125 NC2 N-a-123 CHO1 2ClBn Me Me H 1Me-5- C 448 (M⁺ + 1) 1HIdz N-a-126 NA N-a-125 2ClBn Me H H 1Me-5- C 434 (M⁺ + 1) 1HIdz N-a-127 NC1 Int.n-11 CHO14 2,3DFBn H Me H 1Me-5- C 436 (M⁺ + 1) 1HIdz N-a-128 NA N-a-127 2,3DFBn H H H 1Me-5- C 422 (M⁺ + 1) 1HIdz N-a-129 NC1 Int.n-11 CHO15 3,4DFBn H Me H 1Me-5- C 436 (M⁺ + 1) 1HIdz N-a-130 NA N-a-129 3,4DFBn H H H 1Me-5- C 422 (M⁺ + 1) 1HIdz N-a-131 NC1 Int.n-11 CHO16 4PhBn H Me H 1Me-5- C 476 (M⁺ + 1) 1HIdz N-a-132 NA N-a-131 4PhBn H H H 1Me-5- C 462 (M⁺ + 1) 1HIdz N-a-133 NC1 Int.n-11 CHO19 2-TF H Me H 1Me-5- C 406 (M⁺ + 1) 1HIdz N-a-134 NA N-a-133 2-TF H H H 1Me-5- C 392 (M⁺ + 1) 1HIdz N-a-135 NC1 Int.n-11 CHO17 2CF3Bn H Me H 1Me-5- C 468 (M⁺ + 1) 1HIdz N-a-136 NA N-a-135 2CF3Bn H H H 1Me-5- C 454 (M⁺ + 1) 1HIdz N-a-137 NE1 Int.n-9

H Me H 1Me-5-Ind C 413 (M⁺ + 1) N-a-138 NA N-a-137

H H H 1Me-5-Ind C 399 (M⁺ + 1) N-a-139 NE1 Int.n-11

H Me H 1Me-5-1HIdz D 5.06 414 (M⁺ + 1) N-a-140 NA N-a-139

H H H 1Me-5-1HIdz D 4.30 400 (M⁺ + 1) N-a-141 NE2 Int.n-11 2(4FPh)EtOH 2(4FPh)Et H Me H 1Me-5- D 5.08 432 (M⁺ + 1) 1HIdz N-a-142 NA N-a-141 2(4FPh)Et H H H 1Me-5- D 4.25 418 (M⁺ + 1 1HIdz N-a-143 NF N-a-5 AcCl Bn Ac Me H 1Me-5- C 444 (M⁺ + 1) 1HIdz N-a-144 NA N-a-143 Bn Ac H H 1Me-5- C 430 (M⁺ + 1) 1HIdz N-a-145 NF N-a-5 PhCOCl Bn PhC(O) Me H 1Me-5-Ind C 504 (M⁺ + 1) N-a-146 NA N-a-145 Bn PhC(O) H H 1Me-5-Ind C 490 (M⁺ + 1) N-a-147 NF N-a-5 MeOCH2COCl Bn MeOCH₂C(O) Me H 1Me-5-Ind C 472 (M⁺ + 1) N-a-148 NA N-a-147 Bn MeOCH₂C(O) H H 1Me-5-Ind C 458 (M⁺ + 1) N-a-149 NF N-a-5 MeOCOCl Bn MeOC(O) Me H 1Me-5-Ind C 458 (M⁺ + 1) N-a-150 NA N-a-149 Bn MeOC(O) H H 1Me-5-Ind C 444 (M⁺ + 1) N-a-151 NF N-a-5 PhOCOCl Bn PhOC(O) Me H 1Me-5-Ind C 520 (M⁺ + 1) N-a-152 NA N-a-151 Bn PhOC(O) H H 1Me-5-Ind C 506 (M⁺ + 1) N-a-153 NF N-a-5 NMe2COCl Bn Me₂NC(O) Me H 1Me-5-Ind C 471 (M⁺ + 1) N-a-154 NA N-a-153 Bn Me₂NC(O) H H 1Me-5-Ind C 457 (M⁺ + 1) N-a-155 NF N-a-11 AcCl Bn Ac Me H 1Me-5-Ind C 442 (M⁺ + 1) N-a-156 NA N-a-155 Bn Ac H H 1Me-5-Ind C 428 (M⁺ + 1) N-a-157 NF N-a-5 AcCl 4FBn Ac Me H 1Me-5-Ind C 461 (M⁺ + 1) N-a-158 NA N-a-157 4FBn Ac H H 1Me-5-Ind C 447 (M⁺ + 1) N-a-159 NF N-a-5 MeOCH2COCl 4FBn MeOCH₂C(O) Me H 1Me-5-Ind C 491 (M⁺ + 1) N-a-160 NA N-a-159 4FBn MeOCH₂C(O) H H 1Me-5-Ind C 477 (M⁺ + 1) N-a-161 NF N-a-5 MeOCOCl 4FBn MeOC(O) Me H 1Me-5-Ind C 477 (M⁺ + 1) N-a-162 NA N-a-161 4FBn MeOC(O) H H 1Me-5-Ind C 463 (M⁺ + 1) N-a-163 NF N-a-11 AcCl 4FBn Ac Me H 1Me-5- C 462 (M⁺ + 1) 1HIdz N-a-164 NA N-a-163 4FBn Ac H H 1Me-5- C 448 (M⁺ + 1) 1HIdz N-a-165 NF N-a-11 MeOCOCl 4FBn MeOC(O) Me H 1Me-5- C 478 (M⁺ + 1) 1HIdz N-a-166 NA N-a-185 4FBn MeOC(O) H H 1Me-5- C 464 (M⁺ + 1) 1HIdz

Example N-b-1 Synthesis of methyl 3-[4-(N-methylamino)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-b-1) (Synthesis method ND1)

According to the procedure described in the synthesis method of Intermediate Int. n-7 (Synthesis method ND1) provided that the reaction was carried out for 2 hours, the compound of Example N-a-25 (100.3 mg) and 10% palladium/carbon (10.2 mg) were reacted and treated to obtain the title compound (Compound No. N-b-1, 89.7 mg).

Example N-b-35 Synthesis of methyl 3-[4-(N-ethylamino)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-b-35) (Synthesis method NB1)

According to the procedure described in the synthesis method of the compound of Example N-a-1 (Synthesis method NB1) provided that the reaction was carried out for 17 hours, Intermediate n-12 (99.87 mg), 2-naphthaleneboronic acid (87.3 mg), 2 M aqueous sodium carbonate (350 μl) and (Ph₃P)₄Pd (59.6 mg) were reacted and treated to obtain the title compound (Compound No. N-b-35, 103.5 mg).

Example N-b-79 Synthesis of methyl 3-[4-(N-n-butylamino)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-b-79) (Synthesis method NC2)

According to the procedure described in the synthesis method of Intermediate n-3 provided that the reaction was carried out for 13 hours, Intermediate n-7 (164.7 mg) and n-butylaldehyde (38.5 μl, KANTO), sodium triacetoxyborohydride (138.6 mg) and acetic acid (75 μl) were reacted and treated to obtain the title compound (Compound No. N-b-79, 161.3 mg).

Example N-b-183 Synthesis of methyl 3-[4-(N-acetyl-N-methylamino)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-b-183) (Synthesis method NF)

According to the procedure described in the synthesis method of the compound of Example N-a-143 provided that the reaction was carried out for 18 hours, the compound of Example N-b-1 (22.7 mg), pyridine (23.8/1) and acetyl chloride (40 μl) were reacted and treated to obtain the title compound (Compound No. N-b-183, 16.3 mg).

Example N-b-197 Synthesis of 3-[4-(N-benzoyl-N-methylamino)-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. N-b-197) (Synthesis method NF)

According to the procedure described in the synthesis method of the compound of Example N-a-143 provided that the reaction was carried out for 14 hours, the compound of Example N-b-1 (21.8 mg), pyridine (23.8 μl) and benzoyl chloride (345 μl) were reacted and treated. A solution of the obtained residue in methanol (3 ml) was added with 2 N aqueous sodium hydroxide (100 μl), and stirred at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, then made acidic with 5% aqueous hydrochloric acid under ice cooling, and extracted with dichloromethane (5 ml). The organic layer was washed successively with saturated brine, and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Compound No. N-b-197, 13.5 mg).

Examples N-b-1 to N-b-212

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-B-1 to Table-N-B-5. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-B-1

LCMS Exp. Syn SM1 SM2 Rz Ry Y Zx AR method RTime Mass N-b-1 ND1 N-a-25 Me H Me H 2-Nap C 320 (M⁺ + 1) N-b-2 NA N-b-1 Me H H H 2-Nap C 306 (M⁺ + 1) N-b-3 ND1 N-a-29 Me H Me H 5-Ind C 309 (M⁺ + 1) N-b-4 NA N-b-3 Me H H H 5-Ind C 295 (M⁺ + 1) N-b-5 ND1 N-a-31 Me H Me H 1Me-5-Ind C 323 (M⁺ + 1) N-b-6 NA N-b-5 Me H H H 1Me-5-Ind C 309 (M⁺ + 1) N-b-7 ND1 N-a-69 Me H Me H 5-1HIdz C 310 (M⁺ + 1) N-b-8 NA N-b-7 Me H H H 5-1HIdz C 296 (M⁺ + 1) N-b-9 ND1 N-a-49 Me H Me H 1Me-5-1HIdz C 324 (M⁺ + 1) N-b-10 NA N-b-9 Me H H H 1Me-5-1HIdz C 310 (M⁺ + 1) N-b-11 NC2 N-b-1 CHO1 Me Me Me H 2-Nap C 334 (M⁺ + 1) N-b-12 NA N-b-11 Me Me H H 2-Nap C 320 (M⁺ + 1) N-b-13 NC2 N-b-1 CHO2 Me Et Me H 2-Nap C 348 (M⁺ + 1) N-b-14 NA N-b-13 Me Et H H 2-Nap C 334 (M⁺ + 1) N-b-15 NC2 N-b-3 CHO1 Me Me Me H 5-Ind C 323 (M⁺ + 1) N-b-16 NA N-b-15 Me Me H H 5-Ind C 309 (M⁺ + 1) N-b-17 NC2 N-b-5 CHO1 Me Me H H 1Me-5-Ind C 337 (M⁺ + 1) N-b-18 NA N-b-17 Me Me H H 1Me-5-Ind C 323 (M⁺ + 1) N-b-19 NC2 N-b-9 CHO1 Me Me Me H 1Me-5-1HIdz C 338 (M⁺ + 1) N-b-20 NA N-b-19 Me Me H H 1Me-5-1HIdz C 324 (M⁺ + 1) N-b-21 NB1 Int.n-12 BRA1 Et H Me H 2-Nap C 334 (M⁺ + 1) N-b-22 NA N-b-21 Et H H H 2-Nap C 320 (M⁺ + 1) N-b-23 NB1 Int.n-12 BRA2 Et H Me H 5-Ind C 323 (M⁺ + 1) N-b-24 NA N-b-23 Et H H H 5-Ind C 309 (M⁺ + 1) N-b-25 NB1 Int.n-12 BRA3 Et H Me H 1Me-5-Ind C 337 (M⁺ + 1) N-b-26 NA N-b-25 Et H H H 1Me-5-Ind C 323 (M⁺ + 1) N-b-27 NB1 Int.n-12 BRA4 Et H Me H 1Et-5-Ind C 351 (M⁺ + 1) N-b-28 NA N-b-27 Et H H H 1Et-5-Ind C 337 (M⁺ + 1) N-b-29 NB1 Int.n-12 BRA5 Et H Me H 5-1HIdz C 324 (M⁺ + 1) N-b-30 NA N-b-29 Et H H H 5-1HIdz C 310 (M⁺ + 1) N-b-31 NB1 Int.n-12 BRA6 Et H Me H 1Me-5-1HIdz C 338 (M⁺ + 1) N-b-32 NA N-b-31 Et H H H 1Me-5-1HIdz C 324 (M⁺ + 1) N-b-33 NB1 Int.n-12 BRA7 Et H Me H 1Et-5-Idz C 352 (M⁺ + 1) N-b-34 NA N-b-33 Et H H H 1Et-5-Idz C 338 (M⁺ + 1) N-b-35 NB1 Int.n-12 BRA8 Et H Me H 2Me-5-Idz C 338 (M⁺ + 1) N-b-36 NA N-b-35 Et H H H 2Me-5-Idz C 324 (M⁺ + 1) N-b-37 NB1 Int.n-12 BRA9 Et H Me H 5-Bzt C 341 (M⁺ + 1) N-b-38 NA N-b-37 Et H H H 5-Bzt C 327 (M⁺ + 1) N-b-39 NB1 Int.n-12 BRA10 Et H Me H 3-Qu C 335 (M⁺ + 1) N-b-40 NA N-b-39 Et H H H 3-Qu C 321 (M⁺ + 1) N-b-41 NB1 Int.n-12 BRA11 Et H Me H 6-Qu C 335 (M⁺ + 1) N-b-42 NA N-b-41 Et H H H 6-Qu C 321 (M⁺ + l) N-b-43 NC2 N-b-21 CHO2 Et Et Me H 2-Nap C 362 (M⁺ + 1) N-b-44 NA N-b-43 Et Et H H 2-Nap C 348 (M⁺ + 1) N-b-45 NC2 N-b-25 CHO2 Et Et Me H 1Me-5-Ind C 365 (M⁺ + 1) N-b-46 NA N-b-45 Et Et H H 1Me-5-Ind C 351 (M⁺ + 1) N-b-47 NB1 Int.n-13 nPr H Me H 5-Ind C 337 (M⁺ + 1) N-b-48 NA N-b-47 nPr H H H 5-Ind C 323 (M⁺ + 1) N-b-49 NB1 Int.n-13 nPr H Me H 1Me-5-Ind C 351 (M⁺ + 1) N-b-50 NA N-b-49 nPr H H H 1Me-5-Ind C 337 (M⁺ + 1) N-b-51 NB1 Int.n-13 nPr H Me H 5-1HIdz C 338 (M⁺ + 1) N-b-52 NA N-b-51 nPr H H H 5-1HIdz C 324 (M⁺ + 1) N-b-53 NB1 Int.n-13 nPr H Me H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-54 NA N-b-53 nPr H H H 1Me-51 HIdz C 338 (M⁺ + 1) N-b-55 NC2 N-b-47 CHO1 nPr Me Me H 5-Ind C 351 (M⁺ + 1) N-b-56 NA N-b-55 nPr Me H H 5-Ind C 337 (M⁺ + 1) N-b-57 NC2 N-b-49 CHO1 nPr Me Me H 1Me-5-Ind C 365 (M⁺ + 1) N-b-58 NA N-b-57 nPr Me H H 1Me-5-Ind C 351 (M⁺ + 1) N-b-59 NC2 N-b-51 CHO1 nPr Me Me H 5-1HIdz C 352 (M⁺ + 1) N-b-60 NA N-b-59 nPr Me H H 5-1HIdz C 338 (M⁺ + 1) N-b-61 NC2 N-b-53 CHO1 nPr Me Me H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-62 NA N-b-61 nPr Me H H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-63 NB1 Int.n-14 BRA2 iPr H Me H 5-Ind C 337 (M⁺ + 1) N-b-64 NA N-b-63 iPr H H H 5-Ind C 323 (M⁺ + 1) N-b-65 NB1 Int.n-14 BRA3 iPr H Me H 1Me-5-Ind C 351 (M⁺ + 1) N-b-66 NA N-b-65 iPr H H H 1Me-5-Ind C 337 (M⁺ + 1) N-b-67 NB1 Int.n-14 BRA5 iPr H Me H 5-1HIdz C 338 (M⁺ + 1) N-b-68 NA N-b-67 iPr H H H 5-1HIdz C 324 (M⁺ + 1) N-b-69 NB1 Int.n-14 BRA6 iPr H Me H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-70 NA N-b-69 iPr H H H 1Me-5-1HIdz C 338 (M⁺ + 1) N-b-71 NC2 N-b-63 CHO1 iPr Me Me H 5-Ind C 351 (M⁺ + 1) N-b-72 NA N-b-71 iPr Me H H 5-Ind C 337 (M⁺ + 1) N-b-73 NC2 N-b-65 CHO1 iPr Me Me H 1Me-5-Ind C 365 (M⁺ + 1) N-b-74 NA N-b-73 iPr Me H H 1Me-5-Ind C 351 (M⁺ + 1) N-b-75 NC1 N-b-67 CHO1 iPr Me Me H 5-1HIdz C 352 (M⁺ + 1) N-b-76 NA N-b-75 iPr Me H H 5-1HIdz C 338 (M⁺ + 1) N-b-77 NC1 N-b-69 CHO1 iPr Me Me H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-78 NA N-b-77 iPr Me H H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-79 NB1 Int.n-7 BRA1 nBu H Me H 2-Nap C 362 (M⁺ + 1) N-b-80 NA N-b-79 nBu H H H 2-Nap C 348 (M⁺ + 1) N-b-81 NB1 Int.n-8 BRA2 nBu H Me H 5-Ind C 351 (M⁺ + 1) N-b-82 NA N-b-81 nBu H H H 5-Ind C 337 (M⁺ + 1) N-b-83 NB1 Int.n-10 BRA5 nBu H Me H 5-1HIdz C 352 (M⁺ + 1) N-b-84 NA N-b-83 nBu H H H 5-1HIdz C 338 (M⁺ + 1) N-b-85 NB1 Int.n-11 BRA6 nBu H Me H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-86 NA N-b-85 nBu H H H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-87 NC1 N-b-79 CHO1 nBu Me Me H 2-Nap C 376 (M⁺ + 1) N-b-88 NA N-b-87 nBu Me H H 2-Nap C 351 (M⁺ + 1) N-b-89 NC1 N-b-81 CHO1 nBu Me Me H 5-Ind C 365 (M⁺ + 1) N-b-90 NA N-b-89 nBu Me H H 5-Ind C 351 (M⁺ + 1) N-b-91 NC1 N-b-83 CHO1 nBu Me Me H 5-1HIdz C 366 (M⁺ + 1) N-b-92 NA N-b-91 nBu Me H H 5-1HIdz C 352 (M⁺ + 1) N-b-93 NC1 N-b-85 CHO1 nBu Me Me H 1Me-5-1HIdz C 380 (M⁺ + 1) N-b-94 NA N-b-93 nBu Me H H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-95 NC2 N-b-81 CHO2 nBu Et Me H 5-Ind C 379 (M⁺ + 1) N-b-98 NA N-b-95 nBu Et H H 5-Ind C 365 (M⁺ + 1) N-b-97 NC2 N-b-85 CHO2 nBu Et Me H 1Me-5-1HIdz C 394 (M⁺ + 1) N-b-98 NA N-b-97 nBu Et H H 1Me-5-1HIdz C 380 (M⁺ + 1) N-b-99 NC2 Int.n-9 CHO7 iBu H Me H 1Me-5-Ind C 365 (M⁺ + 1) N-b-100 NA N-b-99 iBu H H H 1Me-5-Ind C 351 (M⁺ + 1) N-b-101 NC2 Int.n-10 CHO7 iBu H Me H 5-1HIdz C 352 (M⁺ + 1) N-b-102 NA N-b-101 iBu H H H 5-1HIdz C 338 (M⁺ + 1) N-b-103 NC2 Int.n-11 CHO7 iBu H Me H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-104 NA N-b-103 iBu H H H 1Me-5-1HIdz C 352 (M⁺ + 1) N-b-105 NC2 Int.n-15 BRA11 iBu H Me H 6-Qu C 363 (M⁺ + 1) N-b-106 NA N-b-105 iBu H H H 6-Qu C 349 (M⁺ + 1) N-b-107 NC1 N-b-99 CHO1 iBu Me Me H 1Me-5-Ind C 379 (M⁺ + 1) N-b-108 NA N-b-107 iBu Me H H 1Me-5-Ind C 365 (M⁺ + 1) N-b-109 NC1 N-b-103 CHO1 iBu Me Me H 1Me-5-1HIdz C 380 (M⁺ + 1) N-b-110 NA N-b-109 iBu Me H H 1Me-5-1HIdz C 366 (M⁺ + 1) N-b-111 NCb N-b-105 CHO1 iBu Me Me H 6-Qu C 377 (M⁺ + 1) N-b-112 NA N-b-111 iBu Me H H 6-Qu C 363 (M⁺ + 1) N-b-113 NC2 N-b-99 CHO2 iBu Et Me H 1Me-5-Ind C 393 (M⁺ + 1) N-b-114 NA N-b-113 iBu Et H H 1Me-5-Ind C 379 (M⁺ + 1) N-b-115 NC2 N-b-101 CHO2 iBu Et Me H 5-1HIdz C 380 (M⁺ + 1) N-b-116 NA N-b-115 iBu Et H H 5-1HIdz C 366 (M⁺ + 1) N-b-117 NC2 N-b-103 CHO2 iBu Et Me H 1Me-5-1HIdz C 394 (M⁺ + 1) N-b-118 NA N-b-117 iBu Et H H 1Me-5-1HIdz C 380 (M⁺ + 1) N-b-119 NB1 Int.n-16 BRA1 cPen H Me H 2-Nap C 374 (M⁺ + l) N-b-120 NA N-b-119 cPen H H H 2-Nap C 360 (M⁺ + 1) N-b-121 NB1 Int.n-16 BRA2 cPen H Me H 5-Ind C 363 (M⁺ + 1) N-b-122 NA N-b-121 cPen H H H 5-Ind C 349 (M⁺ + 1) N-b-123 NB1 Int.n-9 BRA3 cPen H Me H 1Me-5-Ind C 377 (M⁺ + 1) N-b-124 NA N-b-123 cPen H H H 1Me-5-Ind C 363 (M⁺ + l) N-b-125 NB1 Int.n-16 BRA5 cPen H Me H 5-1HIdz C 364 (M⁺ + 1) N-b-126 NA N-b-125 cPen H H H 5-1HIdz C 350 (M⁺ + 1) N-b-127 NB1 Int.n-11 BRA6 cPen H Me H 1Me-5-1HIdz C 378 (M⁺ + 1) N-b-128 NA N-b-127 cPen H H H 1Me-5-1HIdz C 364 (M⁺ + 1) N-b-129 NB1 Int.n-16 BRA11 cPen H Me H 6-Qu C 375 (M⁺ + 1) N-b-130 NA N-b-129 cPen H H H 6-Qu C 361 (M⁺ + 1) N-b-131 NB1 Int.n-16 BRA9 cPen H Me H 5-Bzt C 381 (M⁺ + 1) N-b-132 NA N-b-131 cPen H H H 5-Bzt C 367 (M⁺ + 1) N-b-133 NC1 N-b-121 CHO1 cPen Me Me H 5-Ind C 377 (M⁺ + 1) N-b-134 NA N-b-133 cPen Me H H 5-Ind C 363 (M⁺ + 1) N-b-135 NC1 N-b-123 CHO1 cPen Me Me H 1Me-5-Ind C 391 (M⁺ + 1) N-b-136 NA N-b-135 cPen Me H H 1Me-5-Ind C 377 (M⁺ + 1) N-b-137 NC1 N-b-127 CHO1 cPen Me Me H 1Me-5-1HIdz C 392 (M⁺ + 1) N-b-138 NA N-b-137 cPen Me H H 1Me-5-1HIdz C 378 (M⁺ + 1) N-b-139 NC2 N-b-123 CHO2 cPen Et Me H 1Me-5-Ind C 405 (M⁺ + 1) N-b-140 NA N-b-139 cPen Et H H 1Me-5-Ind C 391 (M⁺ + 1) N-b-141 NC2 N-b-131 CHO2 cPen Et Me H 5-Bzt C 409 (M⁺ + 1) N-b-142 NA N-b-141 cPen Et H H 5-Bzt C 395 (M⁺ + 1) N-b-143 NB1 Int.n-17 BRAl cHex H Me H 2-Nap C 388 (M⁺ + 1) N-b-144 NA N-b-143 cHex H H H 2-Nap C 374 (M⁺ + 1) N-b-145 NB1 Int.n-17 BRA2 cHex H Me H 5-Ind C 377 (M⁺ + 1) N-b-146 NA N-b-145 cHex H H H 5-Ind C 363 (M⁺ + 1) N-b-147 NB1 Int.n-9 BRA3 cHex H Me H 1Me-5-Ind C 391 (M⁺ + 1) N-b-148 NA N-b-147 cHex H H H 1Me-5-Ind C 377 (M⁺ + 1) N-b-149 NB1 Int.n-17 BRA5 cHex H Me H 5-1HIdz C 378 (M⁺ + 1) N-b-150 NA N-b-149 cHex H H H 5-1HIdz C 364 (M⁺ + 1) N-b-151 NB1 Int.n-17 BRA6 cHex H Me H 1Me-5-1HIdz C 392 (M⁺ + 1) N-b-152 NA N-b-151 cHex H H H 1Me-5-1HIdz C 378 (M⁺ + 1) N-b-153 NB1 Int.n-17 BRA10 cHex H Me H 3-Qu C 389 (M⁺ + 1) N-b-154 NA N-b-153 cHex H H H 3-Qu C 375 (M⁺ + 1) N-b-155 NC1 N-b-143 CHO1 cHex Me Me H 2-Nap C 402 (M⁺ + 1) N-b-156 NA N-b-155 cHex Me H H 2-Nap C 388 (M⁺ + 1) N-b-157 NC1 N-b-147 CHO1 cHex Me Me H 1Me-5-Ind C 405 (M⁺ + 1) N-b-158 NA N-b-157 cHex Me H H 1Me-5-Ind C 391 (M⁺ + 1) N-b-159 NC1 N-b-149 CHO1 cHex Me Me H 5-1HIdz C 392 (M⁺ + 1) N-b-160 NA N-b-159 cHex Me H H 5-1 HIdz C 378 (M⁺ + 1) N-b-161 NC1 N-b-151 CHO1 cHex Me Me H 1Me-5-1HIdz C 406 (M⁺ + 1) N-b-162 NA N-b-161 cHex Me H H 1Me-5-1HIdz C 392 (M⁺ + 1) N-b-163 NC2 N-b-143 CHO2 cHex Et Me H 2-Nap C 416 (M⁺ + 1) N-b-164 NA N-b-163 cHex Et H H 2-Nap C 402 (M⁺ + 1) N-b-165 NC2 N-b-153 CHO2 cHex Et Me H 3-Qu C 417 (M⁺ + 1) N-b-166 NA N-b-165 cHex Et H H 3-Qu C 403 (M⁺ + 1) N-b-167 NB1 Int.n-18 BRA2 2(Me) H Me H 5-Ind C 391 (M⁺ + 1) cHex N-b-168 NA N-b-167 2(Me) H H H 5-Ind C 377 (M⁺ + 1) cHex N-b-169 NB1 Int.n-18 BRA3 2(Me) H Me H 1Me-5-Ind C 405 (M⁺ + 1) cHex N-b-170 NA N-b-169 2(Me) H H H 1Me-5-Ind C 391 (M⁺ + 1) cHex N-b-171 NB1 Int.n-18 BRA5 2(Me) H Me H 5-1HIdz C 392 (M⁺ + 1) cHex N-b-172 NA N-b-171 2(Me) H H H 5-1 HIdz C 378 (M⁺ + 1) cHex N-b-173 NB1 Int.n-18 BRA6 2(Me) H Me H 1Me-5-1HIdz C 406 M⁺ + 1) cHex N-b-174 NA N-b-173 2(Me) H H H 1Me-51HIdz C 392 (M⁺ + 1) cHex N-b-175 NC2 Int.n-8 CHO25 2- H Me H 5-Ind C 411 (M⁺ + 1) Indane N-b-176 NA N-b-175 2- H H H 5-Ind C 397 (M⁺ + 1) Indane N-b-177 NC2 Int.n-9 CHO25 2- H Me H 1Me-5-Ind C 425 (M⁺ + 1) Indane N-b-178 NA N-b-177 2- H H H 1Me-5-Ind C 411 (M⁺ + 1) Indane N-b-179 NC2 Int.n-10 CHO25 2- H Me H 5-1HIdz C 412 (M⁺ + 1) Indane N-b-180 NA N-b-179 2- H H H 5-1HIdz C 398 (M⁺ + 1) Indane N-b-181 NC2 Int.n-11 CHO25 2- H Me H 1Me-5-1HIdz C 426 (M⁺ + 1) Indane N-b-182 NA N-b-181 2- H H H 1Me-5-1HIdz C 412 (M⁺ + 1) Indane N-b-183 NF N-b-1 AcCl Me Ac Me H 2-Nap C 364 (M⁺ + 1) N-b-184 NA N-b-183 Me Ac H H 2-Nap C 350 (M⁺ + 1) N-b-185 NF N-b-5 AcCl Me Ac Me H 1Me-5-Ind C 367 (M⁺ + 1) N-b-186 NA N-b-185 Me Ac H H 1Me-5-Ind C 353 (M⁺ + 1) N-b-187 NF N-b-11 AcCl Me Ac Me H 1Me-5-1HIdz C 368 (M⁺ + 1) N-b-188 NA N-b-187 Me Ac H H 1Me-5-1HIdz C 354 (M⁺ + 1) N-b-189 NF Int.n-11 AcCl Ac Ac Me H 1Me-5-1HIdz C 394 (M⁺ + 1) N-b-190 NA N-b-189 Ac Ac H H 1Me-5-1HIdz C 380 (M⁺ + 1) N-b-191 NF Int.n-18 MeOCOCl Me MeOC(O) Me H 2-Nap C 380 (M⁺ + 1) N-b-192 NA N-b-167 Me MeOC(O) H H 2-Nap C 366 (M⁺ + 1) N-b-193 NF Int.n-18 MeOCOCl Me MeOC(O) Me H 1Me-5-Ind C 383 (M⁺ + 1) N-b-194 NA N-b-169 Me MeOC(O) H H 1Me-5-Ind C 369 (M⁺ + 1) N-b-195 NF Int.n-18 MeOCOCl Me MeOC(O) Me H 1Me-5-1HIdz C 384 (M⁺ + 1) N-b-196 NA N-b-171 Me MeOC(O) H H 1Me-5-1HIdz C 370 (M⁺ + 1) N-b-197 NF- N-b-1 BzCl Me Bz H H 2-Nap C 396 (M⁺ + 1) NA N-b-198 NF- N-b-3 BzCl Me Bz H H 5-Ind C 399 (M⁺ + 1) NA N-b-199 NF- N-b-5 BzCl Me Bz H H 1Me-5-Ind C 399 (M⁺ + 1) NA N-b-200 NF- N-b-9 BzCl Me Bz H H 5-1HIdz C 386 (M⁺ + 1) NA N-b-201 NF- N-b-11 BzCl Me Bz H H 1Me-5-1HIdz C 400 (M⁺ + 1) NA N-b-202 NF-NA N-b-1 PhOCOCl Me

H H 2-Nap C 412 (M⁺ + 1) N-b-203 NF-NA N-b-5 PhOCOCl Me

H H 1Me-5-Ind C 415 (M⁺ + 1) N-b-204 NF-NA N-b-1 cPenCH2COCl Me

H H 2-Nap C 402 (M⁺ + 1) N-b-205 NF-NA N-b-3 cPenCH2COCl Me

H H 1Me-5Ind C 405 (M⁺ + 1) N-b-206 NF-NA N-b-1

Me

H H 2-Nap C 403 (M⁺ + 1) N-b-207 NF-NA N-b-5

Me

H H 1Me-5-Ind C 406 (M⁺ + 1) N-b-208 NF- N-b-1 PhNCO Me PhNHC(O) H H 2-Nap C 411 (M⁺ + 1) NA N-b-209 NF- N-b-5 PhNCO Me PhNHC(O) H H 1Me-5-Ind C 414 (M⁺ + 1) NA N-b-210 NF- N-b-1 cHexNCO Me cHexNHC(O) H H 2-Nap C 417 (M⁺ + 1) NA N-b-211 NF- N-b-5 cHexNCO Me cHexNHC(O) H H 1Me-5-Ind C 420 (M⁺+ 1) NA N-b-212 NF- N-b-1 cHexNCS Me PhNHC(S) H H 2-Nap C 430 (M⁺ + 1) NA

Example N-c-51 Synthesis of ethyl 3-[4-(imidazol-1-yl)-3-(naphthalen-2-yl)phenyl]acrylate (Compound No. N-c-51) (Synthesis method NB1)

According to the procedure described in the synthesis method of the compound of Example N-a-1 (Synthesis method NB1) provided that the reaction was carried out for 16 hours, and the column chromatography was performed with chloroform:methanol=100:1, Intermediate n-33 (300.4 mg), 2-naphthaleneboronic acid (208.3 mg), 2 M aqueous sodium carbonate (900 μl) and (Ph₃P)₄Pd (108.3 mg) were reacted and treated to obtain the title compound (Intermediate N-c-51, 304.2 mg).

Example N-c-52 Synthesis of 3-[4-(imidazol-1-yl)-3-(naphthalen-2-yl)phenyl]acrylic acid (Compound No. N-c-51) (Synthesis method NA)

According to the procedure described in the synthesis method of the compound of Example N-a-2 (Synthesis method NA) provided that the reaction was carried out for 2 hours, the compound of Example N-c-51 (301.2 mg) and 2 N aqueous sodium hydroxide (980 μl) were reacted and treated to obtain the title compound (Compound No. N-c-52, 286.4 mg).

Examples N-c-1 to N-c-64

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-C-1 to Table-N-C-3. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-C-1

LCMS Exp. Syn SM1 SM2 NRzRy Y Zx AR method RTime Mass N-c-1 NB1 Int.n-36 BRA1

Me H 2-Nap C 358 (M⁺ + 1) N-c-2 NA N-c-1

H H 2-Nap C 344 (M⁺ + 1) N-c-3 NB1 Int.n-36 BRA2

Me H 5-Ind C 347 (M⁺ + 1) N-c-4 NA N-c-3

H H 5-Ind C 333 (M⁺ + 1) N-c-5 NB1 Int.n-36 BRA3

Me H 1Me-5-Ind C 361 (M⁺ + 1) N-c-6 NA N-c-5

H H 1Me-5-Ind C 347 (M⁺ + 1) N-c-7 NB1 Int.n-36 BRA5

Me H 5-1HIdz C 348 (M⁺ + 1) N-c-8 NA N-c-7

H H 5-1HIdz C 334 (M⁺ + 1) N-c-9 NB1 Int.n-36 BRA6

Me H 1Me-5-1HIdz C 362 (M⁺ + 1) N-c-10 NA N-c-9

H H 1Me-5-1HIdz C 348 (M⁺ + 1) N-c-11 NB1 Int.n-36 BRA9

Me H 5-Bzt C 365 (M⁺ + 1) N-c-12 NA N-c-11

H H 5-Bzt C 351 (M⁺ + 1) N-c-13 NB1 Int.n-36 BRA10

Me H 3-Qu C 359 (M⁺ + 1) N-c-14 NA N-c-13

H H 3-Qu C 345 (M⁺ + 1) N-c-15 NB1 Int.n-36 BRA11

Me H 6-Qu C 359 (M⁺ + 1) N-c-16 NA N-c-15

H H 6-Qu C 345 (M⁺ + 1) N-c-17 NB1 Int.n-37 BRA1

Me H 2-Nap C 374 (M⁺ + 1) N-c-18 NA N-c-17

H H 2-Nap C 360 (M⁺ + 1) N-c-19 NB1 Int.n-37 BRA2

Me H 5-Ind C 363 (M⁺ + 1) N-c-20 NA N-c-19

H H 5-Ind C 349 (M⁺ + 1) N-c-21 NB1 Int.n-37 BRA3

Me H 1Me-5-Ind C 377 (M⁺ + 1) N-c-22 NA N-c-21

H H 1Me-5-Ind C 363 (M⁺ + 1) N-c-23 NB1 Int.n-37 BRA5

Me H 5-1HIdz C 364 (M⁺ + 1) N-c-24 NA N-c-23

H H 5-1HIdz C 350 (M⁺ + 1) N-c-25 NB1 Int.n-37 BRA6

Me H 1Me-5-1HIdz C 378 (M⁺ + 1) N-c-26 NA N-c-25

H H 1Me-5-1HIdz C 364 (M⁺ + 1) N-c-27 NB1 Int.n-26 BRA1

Me H 2-Nap C 372 (M ⁺ + 1) N-c-28 NA N-c-27

H H 2-Nap C 358 (M⁺ + 1) N-c-29 NB1 Int.n-26 BRA2

Me H 5-Ind C 361 (M⁺ + 1) N-c-30 NA N-c-29

H H 5-Ind C 347 (M⁺ + 1) N-c-31 NB1 Int.n-20 BRA3

Me H 1Me-5-Ind C 375 (M⁺ + 1) N-c-32 NA N-c-31

H H 1Me-5-Ind C 361 (M⁺ + 1) N-c-33 NB1 Int.n-26 BRA5

Me H 5-1HIdz C 362 (M⁺ + 1) N-c-34 NA N-c-33

H H 5-1HIdz C 348 (M⁺ + 1) N-c-35 NB1 Int.n-26 BRA6

Me H 1Me-5-1HIdz C 376 (M⁺ + 1) N-c-36 NA N-c-35

H H 1Me-5-1HIdz C 362 (M⁺ + 1) N-c-37 NB1 Int.n-28 BRA1

Me H 2-Nap C 386 (M⁺ + 1) N-c-38 NA N-c-37

H H 2-Nap C 372 (M⁺ + 1) N-c-39 NB1 Int.n-28 BRA3

Me H 1Me-5-Ind C 389 (M⁺ + 1) N-c-40 NA N-c-39

H H 1Me-5-Ind C 375 (M⁺ + 1) N-c-41 NB1 Int.n-28 BRA5

Me H 5-1HIdz C 376 (M⁺ + 1) N-c-42 NA N-c-41

H H 5-1HIdz C 362 (M⁺ + 1) N-c-43 NB1 Int.n-28 BRA6

Me H 1Me-5-1HIdz C 390 (M⁺ + 1) N-c-44 NA N-c-43

H H 1Me-5-1HIdz C 376 (M⁺ + 1) N-c-45 NB1 Int.n-30 BRA3

Me H 1Me-5-Ind C 389 (M⁺ + 1) N-c-46 NA N-c-45

H H 1Me-5-Ind C 375 (M⁺ + 1) N-c-47 NB1 Int.n-30 BRA5

Me H 5-1HIdz C 376 (M⁺ + 1) N-c-48 NA N-c-47

H H 5-1HIdz C 362 (M⁺ + 1) N-c-49 NB1 Int.n-30 BRA6

Me H 1Me-5-1HIdz C 390 (M⁺ + 1) N-c-50 NA N-c-49

H H 1Me-5-1HIdz C 376 (M⁺ + 1) N-c-51 NB1 Int.n-33 BRA1

Et H 2-Nap C 369 (M⁺ + 1) N-c-52 NA N-c-51

H H 2-Nap C 341 (M⁺ + 1) N-c-53 NB1 Int.n-33 BRA3

Et H 1Me-5-Ind C 372 (M⁺ + 1) N-c-54 NA N-c-53

H H 1Me-5-Ind C 344 (M⁺ + 1) N-c-55 NB1 Int.n-33 BRA6

Et H 1Me-5-1HIdz C 373 (M⁺ + 1) N-c-56 NA N-c-55

H H 1Me-5-1HIdz C 345 (M⁺ + 1) N-c-57 NB1 Int.n-35 BRA1

Et H 2-Nap C 368 (M⁺ + 1) N-c-58 NA N-c-57

H H 2-Nap C 340 (M⁺ + 1) N-c-59 NB1 Int.n-35 BRA3

Et H 1Me-5-Ind C 371 (M⁺ + 1) N-c-60 NA N-c-59

H H 1Me-5-Ind C 343 (M⁺ + 1) N-c-61 NB1 Int.n-35 BRA5

Et H 5-1HIdz C 358 (M⁺ + 1) N-c-62 NA N-c-61

H H 5-1HIdz C 330 (M⁺ + 1) N-c-63 NB1 Int.n-35 BRA6

Et H 1Me-51HIdz C 372 (M⁺ + 1) N-c-64 NA N-c-63

H H 1Me-5-1HIdz C 344 (M⁺ + 1)

Example N-d-61 Synthesis of ethyl 3-[4-(imidazol-1-yl)-3-(naphthalen-2-yl)phenyl]propionate (Compound No. N-d-51) (Synthesis method ND1)

According to the procedure described in the synthesis method of Intermediate n-7 (Synthesis method ND1) provided that the reaction was carried out for 6 hours, the compound of Example N-c-51 (301.5 mg) and 10% palladium/carbon (67.3 mg) were reacted and treated to obtain the title compound (Compound No. N-d-61, 143.5 mg).

Example N-d-62 Synthesis of 3-[4-(imidazol-1-yl)-3-(naphthalen-2-yl)phenyl]propionic acid (Compound No. N-d-62) (Synthesis method NA)

According to the procedure described in the synthesis method of the compound of Example N-a-2 (Synthesis method NA) provided that the reaction was carried out for 3 hours, the compound of Example N-d-61 (140.3 mg) and 2 N aqueous sodium hydroxide (600 μl) were reacted and treated to obtain the title compound (Compound No. N-d-62, 100.4 mg).

Examples N-d-1 to N-d-74

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-D-1 to Table-N-D-4. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-D-1

LCMS Exp. Syn SM1 SM2 NRzRy Y Zx AR method RTime Mass N-d-1 NB1 Int.n-21 BRA1

Me H 2-Nap C 360 (M⁺ + 1) N-d-2 NA N-d-1

H H 2-Nap C 346 (M⁺ + 1) N-d-3 NB1 Int.n-21 BRA2

Me H 5-Ind D 4.79 349 (M⁺ + 1) N-d-4 NA N-d-3

H H 5-Ind D 3.54 335 (M⁺ + 1) N-d-5 NB1 Int.n-21 BRA3

Me H 1Me-5-Ind D 5.72 363 (M⁺ + 1) N-d-6 NA N-d-5

H H 1Me-5-Ind D 4.31 349 (M⁺ + 1) N-d-7 NB1 Int.n-21 BRA5

Me H 5-1HIdz C 350 (M⁺ + 1) N-d-8 NA N-d-7

H H 5-1HIdz C 336 (M⁺ + 1) N-d-9 NB1 Int.n-21 BRA6

Me H 1Me-5-1HIdz C 364 (M⁺ + 1) N-d-10 NA N-d-9

H H 1Me-5-1HIdz C 350 (M⁺ + 1) N-d-11 NB1 Int.n-21 BRA9

Me H 5-Bzt C 367 (M⁺ + 1) N-d-12 NA N-d-11

H H 5-Bzt C 353 (M⁺ + 1) N-d-13 NB1 Int.n-21 BRA10

Me H 3-Qu C 361 (M⁺ + 1) N-d-14 NA N-d-13

H H 3-Qu C 347 (M⁺ + 1) N-d-15 NB1 Int.n-21 BRA11

Me H 6-Qu C 361 (M⁺ + 1) N-d-16 NA N-d-15

H H 6-Qu C 347 (M⁺ + 1) N-d-17 NB1 Int.n-24 BRA1

NMe H 2-Nap C 376 (M⁺ + 1) N-d-18 NA N-d-17

H H 2-Nap C 362(M⁺ + 1) N-d-19 NB1 Int.n-24 BRA2

Me H 5-Ind C 365 (M⁺ + 1) N-d-20 NA N-d-19

H H 5-Ind C 351 (M⁺ + 1) N-d-21 NB1 Int.n-24 BRA3

Me H 1Me-5-Ind C 379 (M⁺ + 1) N-d-22 NA N-d-21

H H 1Me-5-Ind C 365 (M⁺ + 1) N-d-23 NB1 Int.n-24 BRA5

Me H 5-1HIdz C 366 (M⁺ + 1) N-d-24 NA N-d-23

H H 5-1HIdz C 352 (M⁺ + 1) N-d-25 NB1 Int.n-24 BRA6

Me H 1Me-5-1HIdz C 380 (M⁺ + 1) N-d-26 NA N-d-25

H H 1Me-5-1HIdz C 366 (M⁺ + 1) N-d-27 NB1 Int.n-24 BRA9

Me H 5-Bzt C 383 (M⁺ + 1) N-d-28 NA N-d-27

H H 5-Bzt C 369 (M⁺ + 1) N-d-29 NB1 Int.n-24 BRA11

Me H 6-Qu C 377 (M⁺ + 1) N-d-30 NA N-d-29

H H 6-Qu C 363 (M⁺ + 1) N-d-31 NB1 Int.n-27 BRA1

Me H 2-Nap C 374 (M⁺ + 1) N-d-32 NA N-d-31

H H 2-Nap C 360 (M⁺ + 1) N-d-33 NB1 Int.n-27 BRA2

Me H 5-Ind C 363 (M⁺1) N-d-34 NA N-d-33

H H 5-Ind C 349 (M⁺ + 1) N-d-35 NB1 Int.n-27 BRA3

Me H 1Me-5-Ind C 377 (M⁺ + 1) N-d-36 NA N-d-35

H H 1Me-5-Ind C 363 (M⁺ + 1) N-d-37 NB1 Int.n-27 BRA5

Me H 5-1HIdz C 364 (M⁺ + 1) N-d-38 NA N-d-37

H H 5-1HIdz C 350 (M⁺ + 1) N-d-39 NB1 Int.n-27 BRA6

Me H 1Me-5-1HIdz C 378 (M⁺ + 1) N-d-40 NA N-d-39

H H 1Me-5-1HIdz C 364 (M⁺ + 1) N-d-41 NB1 Int.n-27 BRA11

Me H 6-Qu C 375 (M⁺ + 1) N-d-42 NA N-d-41

H H 6-Qu C 361 (M⁺ + 1) N-d-43 NB1 Int.n-27 BRA9

Me H 5-Bzt C 381 (M⁺ + 1) N-d-44 NA

N-d-43 H H 5-Bzt C 367 (M⁺ + 1) N-d-45 NB1 Int.n-29 BRA1

Me H 2-Nap C 388 (M⁺ + 1) N-d-46 NA N-d-45

H H 2-Nap C 374 (M⁺ + 1) N-d-47 NB1 Int.n-29 BRA3

Me H 1Me-5Ind C 391 (M⁺ + 1) N-d-48 NA N-d-47

H H 1Me-5-Ind C 377 (M⁺ + 1) N-d-49 NB1 Int.n-29 BRA5

Me H 5-1Idz C 378 (M⁺ + 1) N-d-50 NA N-d-49

H H 5-1Idz C 364 (M⁺ + 1) N-d-51 NB1 Int.n-29 BRA6

Me H 1Me-5-1HIdz C 392 (M⁺ + 1) N-d-52 NA N-d-51

H H 1Me-5-1HIdz C 378 (M⁺ + 1) N-d-53 NB1 Int.n-29 BRA10

Me H 3-Qu C 389 (M⁺ + 1) N-d-54 NA N-d-53

H H 3-Qu C 375 (M⁺ + 1) N-d-55 NB1 Int.n-31 BRA3

Me H 1Me-5-Ind C 391 (M⁺ + 1) N-d-56 NA N-d-55

H H 1Me-5-Ind C 377 (M⁺ + 1) N-d-57 NB1 Int.n-31 BRA5

Me H 5-1Idz C 378 (M⁺ + 1) N-d-58 NA N-d-57

H H 5-1Idz C 364 (M⁺ + 1) N-d-59 NB1 Int.n-31 BRA6

Me H 1Me-5-1HIdz C 392 (M⁺ + 1) N-d-60 NA N-d-59

H H 1Me-5-1HIdz C 378 (M⁺ + 1) N-d-61 ND1 N-c-51

Et H 2-Nap C 371 (M⁺ + 1) N-d-62 NA N-d-61

H H 2-Nap C 343 (M⁺ + 1) N-d-63 ND1 N-c-53

Et H 1Me-5-Ind C 374 (M⁺ + 1) N-d-64 NA N-d-63

H H 1Me-5-Ind C 346 (M⁺ + 1) N-d-65 ND1 N-c-55

Et H 1Me-5-1HIdz C 375 (M⁺ + 1) N-d-66 NA N-d-65

H H 1Me-5-1HIdz C 347 (M⁺ + 1) N-d-67 ND1 N-c-57

Et H 2-Nap C 370 (M⁺ + 1) N-d-68 NA N-d-45

H H 2-Nap C 342 (M⁺ + 1) N-d-69 ND1 N-c-59

Et H 1Me-5-Ind C 373 (M⁺ + 1) N-d-70 NA N-d-47

H H 1Me-5-Ind C 345 (M⁺ + 1) N-d-71 ND1 N-c-61

Et H 5-1Idz C 360 (M⁺ + 1) N-d-72 NA N-d-49

H H 5-1Idz C 332 (M⁺ + 1) N-d-73 ND1 N-c-63

Et H 1Me-5-1HIdz C 374 (M⁺ + 1) N-d-74 NA N-d-51

H H 1Me-5-1HIdz C 346 (M⁺ + 1)

Examples N-e-1 to N-e-204

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-N-E-1 to Table-N-E-7. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, corresponding methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-E-1

LCMS Exp. Syn SM1 SM2 NRzRy Y AR method RTime Mass N-e-1 NB1 Int.n-48 BRA1

Et 2-Nap C 389 (M⁺ + 1) N-e-2 NA N-e-1

H 2-Nap C 375 (M⁺ + 1) N-e-3 NB1 Int.n-48 BRA2

Et 5-Ind C 378 (M⁺ + 1) N-e-4 NA N-e-3

H 5-Ind C 364 (M⁺ + 1) N-e-5 NB1 Int.n-48 BRA3

Et 1Me-5-Ind C 392 (M⁺ + 1) N-e-6 NA N-e-5

H 1Me-5-Ind C 378 (M⁺ + 1) N-e-7 NB1 Int.n-48 BRA5

Et 5-1HIdz C 379 (M⁺ + 1) N-e-8 NA N-e-7

H 5-1HIdz C 365 (M⁺ + 1) N-e-9 NB1 Int.n-48 BRA6

Et 1Me-5-1HIdz C 393 (M⁺ + 1) N-e-10 NA N-e-9

H 1Me-5-1HIdz C 379 (M⁺ + 1) N-e-11 NB1 Int.n-48 BRA10

Et 3-Qu C 390 (M⁺ + 1) N-e-12 NA N-c-11

H 3-Qu C 376 (M⁺ + 1) N-e-13 NB1 Int.n-48 BRA11

Et 6-Qu C 390 (M⁺ + 1) N-e-14 NA N-e-13

H 6-Qu C 376 (M⁺ + 1) N-e-15 NB1 Int.n-48 BRA12

Et 6-IQ C 390 (M⁺ + 1) N-e-16 NA N-e-15

H 6-IQ C 376 (M⁺ + 1) N-e-17 NB1 Int.n-49 BRA1

Et 2-Nap C 375 (M⁺ + 1) N-e-18 NA N-e-17

H 2-Nap C 361 (M⁺ + 1) N-e-19 NB1 Int.n-49 BRA2

Et 5-Ind C 364 (M⁺ + 1) N-e-20 NA N-e-19

H 5-Ind C 350 (M⁺ + 1) N-e-21 NB1 Int.n-49 BRA3

Et 1Me-5-Ind C 378 (M⁺ + 1) N-e-22 NA N-e-21

H 1Me-5-Ind C 364 (M⁺ + 1) N-e-23 NB1 Int.n-49 BRA5

Et 5-1HIdz C 365 (M⁺ + 1) N-e-24 NA N-e-23

H 5-1HIdz C 351 (M⁺ + 1) N-e-25 NB1 Int.n-49 BRA6

Et 1Me-5-1HIdz C 379 (M⁺ + 1) N-e-26 NA N-e-25

H 1Me-5-1HIdz C 365 (M⁺ + 1) N-e-27 NB1 Int.n-50 BRA1

Et 2-Nap C 403 (M⁺ + 1) N-e-28 NA N-e-27

H 2-Nap C 389 (M⁺ + 1) N-e-29 NB1 Int.n-50 BRA2

Et 5-Ind C 392 (M⁺ + 1) N-e-30 NA N-e-29

H 5-Ind C 378 (M⁺ + 1) N-e-31 NB1 Int.n-50 BRA3

Et 1Me-5-Ind C 406 (M⁺ + 1) N-e-32 NA N-e-31

H 1Me-5-Ind C 392 (M⁺ + 1) N-e-33 NB1 Int.n-50 BRA5

Et 5-1HIdz C 393 (M⁺ + 1) N-e-34 NA N-e-33

H 5-1HIdz C 379 (M⁺ + 1) N-e-35 NB1 Int.n-50 BRA6

Et 1Me-5-1HIdz C 407 (M⁺ + 1) N-e-36 NA N-e-35

H 1Me-5-1HIdz C 393 (M⁺ + 1) N-e-37 NB1 Int.n-51 BRA1

Et 2-Nap C 391 (M⁺ + 1) N-e-38 NA N-e-37

H 2-Nap C 377 (M⁺ + 1) N-e-39 NB1 Int.n-51 BRA3

Et 1Me-5-Ind C 394 (M⁺ + 1) N-e-40 NA N-e-39

H 1Me-5-Ind C 380 (M⁺ + 1) N-e-41 NB1 Int.n-51 BRA5

Et 5-1HIdz C 381 (M⁺ + 1) N-e-42 NA N-e-41

H 5-1HIdz C 367 (M⁺ + 1) N-e-43 NB1 Int.n-51 BRA6

Et 1Me-5-1HIdz C 395 (M⁺ + 1) N-e-44 NA N-e-43

H 1Me-5-1HIdz C 381 (M⁺ + 1) N-e-45 NB1 Int.n-52 BRA1

Et 2-Nap C 403 (M⁺ + 1) N-e-46 NA N-e-45

H 2-Nap C 389 (M⁺ + 1) N-e-47 NB1 Int.n-52 BRA3

Et 1Me-5-Ind C 406 (M⁺ + 1) N-e-48 NA N-e-47

H 1Me-5-Ind C 392 (M⁺ + 1) N-e-49 NB1 Int.n-52 BRA5

Et 5-1HIdz C 393 (M⁺ + 1) N-e-50 NA N-e-49

H 5-1HIdz C 379 (M⁺ + 1) N-e-51 NB1 Int.n-52 BRA6

Et 1Me-5-1HIdz C 407 (M⁺ + 1) N-e-52 NA N-e-51

H 1Me-5-1HIdz C 393 (M⁺ + 1)

TABLE N-E-4

LCMS Exp. Syn SM1 SM2 Rz Ry Y AR method RTime Mass N-e-53 NB1 Int.n-53 BRA1 Et Me Et 2-Nap C 363 (M⁺ + 1) N-e-54 NA N-e-53 Et Me H 2-Nap C 335 (M⁺ + 1) N-e-55 NB1 Int.n-53 BRA2 Et Me Et 5-Ind C 352 (M⁺ + 1) N-e-56 NA N-e-55 Et Me H 5-Ind C 324 (M⁺ + 1) N-e-57 NB1 Int.n-53 BRA3 Et Me Et 1Me-5-Ind C 366 (M⁺ + 1) N-e-58 NA N-e-57 Et Me H 1Me-5-Ind C 338 (M⁺ + 1) N-e-59 NB1 Int.n-53 BRA5 Et Me Et 5-1HIdz C 353 (M⁺ + 1) N-e-60 NA N-e-59 Et Me H 5-1HIdz C 325 (M⁺ + 1) N-e-61 NB1 Int.n-53 BRA6 Et Me Et 1Me-5-1HIdz C 367 (M⁺ + 1) N-e-62 NA N-e-61 Et Me H 1Me-5-1HIdz C 339 (M⁺ + 1) N-e-63 NB1 Int.n-54 BRA1 Et Et Et 2-Nap C 377 (M⁺ + 1) N-e-64 NA N-b-63 Et Et H 2-Nap C 349 (M⁺ + 1) N-e-65 NB1 Int.n-54 BRA2 Et Et Et 5-Ind C 366 (M⁺ + 1) N-e-66 NA N-b-65 Et Et H 5-Ind C 338 (M⁺ + 1) - N-e-67 NB1 Int.n-54 BRA3 Et Et Et 1Me-5-Ind C 380 (M⁺ + 1) N-e-68 NA N-b-67 Et Et H 1Me-5-Ind C 352 (M⁺ + 1) N-e-69 NB1 Int.n-54 BRA5 Et Et Et 5-1HIdz C 367 (M⁺ + 1) N-e-70 NA N-b-69 Et Et H 5-1HIdz C 339 (M⁺ + 1) N-e-71 NB1 Int.n-54 BRA6 Et Et Et 1Me-5-1HIdz C 381 (M⁺ + 1) N-e-72 NA N-b-71 Et Et H 1Me-5-1HIdz C 353 (M⁺ + 1) N-e-73 NB1 Int.n-55 BRA1 nPr Me Et 2-Nap C 377 (M⁺ + 1) N-e-74 NA N-b-73 nPr Me H 2-Nap C 349 (M⁺ + 1) N-e-75 NB1 Int.n-55 BRA2 nPr Me Et 5-Ind C 366 (M⁺ + 1) N-e-76 NA N-b-75 nPr Me H 5-Ind C 338 (M⁺ + 1) N-e-77 NB1 Int.n-55 BRA3 nPr Me Et IMe-5-Ind C 380 (M⁺ + 1) N-e-78 NA N-b-77 nPr Me H 1Me-5-Ind C 352 (M⁺ + 1) N-e-79 NB1 Int.n-55 BRA5 nPr Me Et 5-1HIdz C 367 (M⁺ + 1) N-e-80 NA N-b-79 nPr Me H 5-1HIdz C 339 (M⁺ + 1) N-e-81 NB1 Int.n-55 BRA6 nPr Me Et 1Me-5-1HIdz C 381 (M⁺ + 1) N-e-82 NA N-b-81 nPr Me H 1Me-5-1HIdz C 353 (M⁺ + 1) N-e-83 NB1 Int.n-56 BRA1 iPr Me Et 2-Nap C 377 (M⁺ + 1) N-e-84 NA N-b-83 iPr Me H 2-Nap C 349 (M⁺ + 1) N-e-85 NB1 Int.n-56 BRA2 iPr Me Et 5-Ind C 366 (M⁺ + 1) N-e-86 NA N-b-85 iPr Me H 5-Ind C 338 (M⁺ + 1) N-e-87 NB1 Int.n-56 BRA3 iPr Me Et 1Me-5-Ind C 380 (M⁺ + 1) N-e-88 NA N-b-87 iPr Me H 1Me-5-Ind C 352 (M⁺ + 1) N-e-89 NB1 Int.n-56 BRA5 iPr Me Et 5-1HIdz C 367 (M⁺ + 1) N-e-90 NA N-b-89 iPr Me H 5-1HIdz C 339 (M⁺ + 1) N-e-91 NB1 Int.n-56 BRA6 iPr Me Et 1Me-5-1HIdz C 381 (M⁺ + 1) N-e-92 NA N-b-91 iPr Me H 1Me-5-1HIdz C 353 (M⁺ + 1) N-e-93 NB1 Int.n-57 BRA1 nBu Me Et 2-Nap C 391 (M⁺ + 1) N-e-94 NA N-b-93 nBu Me H 2-Nap C 363 (M⁺ + 1) N-e-95 NB1 Int.n-57 BRA2 nBu Me Et 5-Ind C 380 (M⁺ + 1) N-e-96 NA N-b-95 nBu Me H 5-Ind C 352 (M⁺ + 1) N-e-97 NB1 Int.n-57 BRA3 nBu Me Et 1Me-5-Ind C 394 (M⁺ + 1) N-e-98 NA N-e-97 nBu Me H 1Me-5-Ind C 366 (M⁺ + 1) N-e-99 NB1 Int.n-57 BRA5 nBu Me Et 5-1HIdz C 381 (M⁺ + 1) N-e-100 NA N-e-99 nBu Me H 5-1HIdz C 353 (M⁺ + 1) N-e-101 NB1 Int.n-57 BRA6 nBu Me Et 1Me-5-1HIdz C 395 (M⁺ + 1) N-e-102 NA N-e-101 nBu Me H 1Me-5-1HIdz C 367 (M⁺ + 1) N-e-103 NB1 Int.n-58 BRA1 iBu Me Et 2-Nap C 391 (M⁺ + 1) N-e-104 NA N-e-103 iBu Me H 2-Nap C 363 (M⁺ + 1) N-e-105 NB1 Int.n-58 BRA2 iBu Me Et 5-Ind C 380 (M⁺ + 1) N-e-106 NA N-e-105 iBu Me H 5-Ind C 352 (M⁺ + 1) N-e-107 NB1 Int.n-58 BRA3 iBu Me Et 1Me-5-Ind C 394 (M⁺ + 1) N-e-108 NA N-e-107 iBu Me H 1Me-5-Ind C 366 (M⁺ + 1) N-e-109 NB1 Int.n-58 BRA5 iBu Me Et 5-1HIdz C 381 (M⁺ + 1) N-e-110 NA N-e-109 iBu Me H 5-1HIdz C 353 (M⁺ + 1) N-e-111 NB1 Int.n-58 BRA5 iBu Me Et 1Me-5-1HIdz C 395 (M⁺ + 1) N-e-112 NA N-e-111 iBu Me H 1Me-5-1HIdz C 367 (M⁺ + 1) N-e-113 NB1 Int.n-62 BRA1 Bn H Et 2-Nap C 411 (M⁺ + 1) N-e-114 NA N-e-113 Bn H H 2-Nap C 383 (M⁺ + 1) N-e-115 NB1 Int.n-62 BRA2 Bn H Et 5-Ind C 400 (M⁺ + 1) N-e-116 NA N-e-115 Bn H H 5-Ind C 372 (M⁺ + 1) N-e-117 NB1 Int.n-62 BRA3 Bn H Et 1Me-5-Ind C 414 (M⁺ + 1) N-e-118 NA N-e-117 Bn H H 1Me-5-Ind C 386 (M⁺ + 1) N-e-119 NB1 Int.n-62 BRA5 Bn H Et 5-1HIdz C 401 (M⁺ + 1) N-e-120 NA N-e-119 Bn H H 5-1HIdz C 373 (M⁺ + 1) N-e-121 NB1 Int.n-62 BRA6 Bn H Et 1Me-5-1HIdz C 415 (M⁺ + l) N-e-122 NA N-e-121 Bn H H 1Me-5-1HIdz C 387 (M⁺ + 1) N-e-123 NB1 Int.n-63 BRA1 4MeBn H Et 2-Nap C 425 (M⁺ + 1) N-e-124 NA N-e-123 4MeBn H H 2-Nap C 397 (M⁺ + 1) N-e-125 NB1 Int.n-63 BRA2 4MeBn Me Et 5-Ind C 414 (M⁺ + 1) N-e-126 NA N-e-125 4MeBn Me H 5-Ind C 386 (M⁺ + 1) N-e-127 NB1 Int.n-63 BRA5 4MeBn Me Et 5-1HIdz C 415 (M⁺ + l) N-e-128 NA N-e-127 4MeBn Me H 5-1HIdz C 387 (M⁺ + l) N-e-129 NB1 Int.n-64 BRA2 3MeBn Me Et 5-Ind C 414 (M⁺ + 1) N-e-130 NA N-e-129 3MeBn Me H 5-Ind C 386 (M⁺ + 1) N-e-131 NB1 Int.n-64 BRA3 3MeBn Me Et 1Me-5-Ind C 428 (M⁺ + 1) N-e-132 NA N-e-131 3MeBn Me H 1Me-5-Ind C 400 (M⁺ + 1) N-e-133 NB1 Int.n-64 BRA5 3MeBn Me Et 5-1HIdz C 415 (M⁺ + 1) N-e-134 NA N-e-133 3MeBn Me H 5-1HIdz C 387 (M⁺ + 1) N-e-135 N81 Int.n-65 BRA1 2MeBn Me Et 2-Nap C 425 (M⁺ + 1) N-e-136 NA N-e-135 2MeBn Me H 2-Nap C 397 (M⁺ + 1) N-e-137 NB1 Int.n-65 BRA3 2MeBn Me Et 1Me-5-Ind C 428 (M⁺ + 1) N-e-138 NA N-e-137 2MeBn Me H 1Me-5-Ind C 400 (M⁺ + 1) N-e-139 NB1 Int.n-65 BRA6 2MeBn Me Et 1Me-5-1HIdz C 429 (M⁺ + 1) N-e-140 NA N-e-139 2MeBn Me H 1Me-5-1HIdz C 401 (M⁺ + 1) N-e-141 NB1 Int.n-66 BRA1 4FBn H Et 2-Nap C 429 (M⁺ + 1) N-e-142 NA N-e-141 4FBn H H 2-Nap C 401 (M⁺ + 1) N-e-143 NB1 Int.n-66 BRA3 4FBn H Et 1Me-5-Ind C 432 (M⁺ + 1) N-e-144 NA N-e-143 4FBn H H 1Me-5-Ind C 404 (M⁺ + 1) N-e-145 NB1 Int.n-66 BRA6 4FBn H Et 1Me-5-1HIdz C 433 (M⁺ + 1) N-e-146 NA N-e-145 4FBn H H 1Me-5-1HIdz C 405 (M⁺ + 1) N-e-147 NB1 Int.n-67 BRA1 3FBn H Et 2-Nap C 429 (M⁺ + 1) N-e-148 NA N-e-147 3FBn H H 2-Nap C 401 (M⁺ + 1) N-e-149 NB1 Int.n-67 BRA2 3FBn H Et 5-Ind C 418 (M⁺ + 1) N-e-150 NA N-e-149 3FBn H H 5-Ind C 390 (M⁺ + 1) N-e-151 NB1 Int.n-67 BRA3 3FBn H Et 1Me-5-Ind C 432 (M⁺ + 1) N-e-152 NA N-e-151 3FBn H H 1Me-5-Ind C 404 (M⁺ + 1) N-e-153 NB1 Int.n-68 BRA3 2FBn H Et 1Me-5-Ind C 432 (M⁺ + 1) N-e-154 NA N-e-153 2FBn H H 1Me-5-Ind C 404 (M⁺ + 1) N-e-155 NBI Int.n-68 BRA5 2FBn H Et 5-1HIdz C 419 (M⁺ + 1) N-e-156 NA N-e-155 2FBn H H 5-1HIdz C 391 (M⁺ + 1) N-e-157 NB1 Int.n-68 BRA6 2FBn H Et 1Me-5-1HIdz C 433 (M⁺ + 1) N-e-158 NA N-e-157 2FBn H H 1Me-5-1HIdz C 405 (M⁺ + 1) N-e-159 NB1 Int.n-69 BRA1 4MeOPh H Et 2-Nap C 427 (M⁺ + 1) N-e-160 NA N-e-159 4MeOPh H H 2-Nap C 399 (M⁺ + 1) N-e-161 NB1 Int.n-69 BRA2 4MeOPh H Et 5-Ind C 416 (M⁺ + 1) N-e-162 NA N-e-161 4MeOPh H H 5-Ind C 388 (M⁺ + 1) N-e-163 NB1 Int.n-69 BRA3 4MeOPh H Et 1Me-5-Ind C 430 (M⁺ + 1) N-e-164 NA N-e-163 4MeOPh H H 1Me-5-Ind C 402 (M⁺ + 1) N-e-165 NB1 Int.n-69 BRA5 4MeOPh H Et 5-1HIdz C 417 (M⁺ + 1) N-e-166 NA N-e-165 4MeOPh H H 5-1HIdz C 389 (M⁺ + 1) N-e-167 NB1 Int.n-70 BRA1 3MeOPh H Et 2-Nap C 427 (M⁺ + 1) N-e-168 NA N-e-167 3MeOPh H H 2-Nap C 399 (M⁺ + 1) N-e-169 NB1 Int.n-70 BRA3 3MeOPh H Et 1Me-5-Ind C 430 (M⁺ + 1) N-e-170 NA N-e-169 3MeOPh H H 1Me-5-Ind C 402 (M⁺ + 1) N-e-171 NB1 Int.n-70 BRA5 3MeOPh H Et 1Me-5-1HIdz C 431 (M⁺ + 1) N-e-172 NA N-e-171 3MeOPh H H 1Me-5-1HIdz C 403 (M⁺ + 1) N-e-173 NB1 Int.n-71 BRA5 2MeOPh H Et 5-1HIdz C 417 (M⁺ + 1) N-e-174 NA N-e-173 2MeOPh H H 51 HIdz C 389 (M⁺ + 1) N-e-175 NB1 Int.n-71 BRA5 2MeOPh H Et 1Me-5-1HIdz C 431 (M⁺ + 1) N-e-176 NA N-e-175 2MeOPh H H 1Me-5-1 HIdz C 403 (M⁺ + 1) N-e-177 NB1 Int.n-71 BRA11 2MeOPh H Et 6-Qu C 428 (M⁺ + 1) N-e-178 NA N-e-177 2MeOPh H H 6-Qu C 400 (M⁺ + 1) N-e-179 NB1 Int.n-72 BRA1 4CF3Ph H Et 2-Nap C 465 (M⁺ + 1) N-e-180 NA N-e-179 4CF3Ph H H 2-Nap C 437 (M⁺ + 1) N-e-181 NB1 Int.n-72 BRA3 4CF3Ph H Et 1Me-5-Ind C 468 (M⁺ + 1) N-e-182 NA N-e-181 4CF3Ph H H 1Me-5-Ind C 440 (M⁺ + 1) N-e-183 NB1 Int.n-72 BRA5 4CF3Ph H Et 5-1HIdz C 455 (M⁺ + 1) N-e-184 NA N-e-183 4CF3Ph H H 5-1HIdz C 427 (M⁺ + 1) N-e-185 NB1 Int.n-72 BRA6 4CF3Ph H Et 1Me-5-1HIdz C 469 (M⁺ + 1) N-e-186 NA N-e-185 4CF3Ph H H 1Me-5-1HIdz C 441 (M⁺ + 1) N-e-187 NB1 Int.n-73 BRA1 2EtOPh H Et 2-Nap C 441 (M⁺ + 1) N-e-188 NA N-e-187 2EtOPh H H 2-Nap C 413 (M⁺ + 1) N-e-189 NB1 Int.n-13 BRA3 2EtOPh H Et 1Me-5-Ind C 444 (M⁺ + 1) N-e-190 NA N-e-189 2EtOPh H H 1Me-5-Ind C 416 (M⁺ + 1) N-e-191 NB1 Int.n-73 BRA6 2EtOPh H Et 1Me-5-1HIdz C 445 (M⁺ + 1) N-e-192 NA N-e-191 2EtOPh H H 1Me-5-1HIdz C 417 (M⁺ + 1) N-e-193 NB1 Int.n-74 BRA1 3iPrOPh H Et 2-Nap C 455 (M⁺ + 1) N-e-194 NA N-e-193 3iPrOPh H H 2-Nap C 427 (M⁺ + 1) N-e-195 NB1 Int.n-74 BRA2 3iPrOPh H Et 5-Ind C 444 (M⁺ + 1) N-e-196 NA N-e-195 3iPrOPh H H 5-Ind C 416 (M⁺ + 1) N-e-197 NB1 Int.n-74 BRA3 3iPrOPh H Et 1Me-5-Ind C 458 (M⁺ + 1) N-e-198 NA N-b-197 3iPrOPh H H 1Me-5-Ind C 430 (M⁺ + 1) N-e-199 NB1 Int.n-75 BRA3 3,5DFPh H Et 1Me-5-Ind C 436 (M⁺ + 1) N-e-200 NA N-b-199 3,5DFPh H H 1Me-5-Ind C 408 (M⁺ + 1) N-e-201 NB1 Int.n-75 BRA5 3,5DFPh H Et 5-1HIdz C 423 (M⁺ + 1) N-e-202 NA N-b-201 3,5DFPh H H 5-1HIdz C 395 (M⁺ + 1) N-e-203 NB1 Int.n-75 BRA5 3,5DFPh H Et 1Me-5-1HIdz C 437 (M⁺ + 1) N-e-204 NA N-b-203 3,5DFPh H H 1Me-5-1HIdz C 409 (M⁺ + 1)

Example N-f-1 Synthesis of methyl 3-[3-(naphthalen-2-yl)-4-(N-phenylamino)phenyl]propionate (Compound No. N-f-1) (Synthesis method NB2)

A solution of Intermediate n-7 (306.1 mg) in dehydrated toluene (1 ml) was added with aniline (1 ml, TCI), palladium acetate (20.2 mg, WAKO), 2-(di-t-butylphosphine)biphenyl (39 mg, Across) and cesium carbonate (863.4 mg, WAKO), and stirred at 90° C. for 18 hours. The reaction mixture was added with ethyl acetate (40 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=4:1) to obtain the title compound (Compound No. N-f-1, 101.4 mg).

Examples N-f-1 to N-f-92

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-F-1 and Table-N-F-2. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, corresponding methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-F-1

LCMS Exp. Syn SM1 SM2 Rz Ry Y AR method RTime Mass N-f-1 NB2 Int.n-7 BRA14 Ph H Me 2-Nap C 383 (M⁺ + 1) N-f-2 NA N-f-1 Ph H H 2-Nap C 369 (M⁺ + 1) N-f-3 NB2 Int.n-8 BRA14 Ph H Me 5-Ind C 372 (M⁺ + 1) N-f-4 NA N-f-3 Ph H H 5-Ind C 358 (M⁺ + 1) N-f-5 NB2 Int.n-9 BRA14 Ph H Me 1Me-5Ind C 386 (M⁺ + l) N-f-6 NA N-f-5 Ph H H 1Me-5-Ind C 372 (M⁺ + 1) N-f-7 NB2 Int.n-10 BRA14 Ph H Me 5-1HIdz C 373 (M⁺ + 1) N-f-8 NA N-f-7 Ph H H 5-1HIdz C 359 (M⁺ + 1) N-f-9 NB2 Int.n-11 BRA14 Ph H Me 1Me-5-1HIdz C 387 (M⁺ + 1) N-f-10 NA N-f-9 Ph H H 1Me-5-1HIdz C 373 (M⁺ + l) N-f-11 NB2 N-f-1 CHO1 Ph Me Me 2-Nap C 397 (M⁺ + 1) N-f-12 NA N-f-11 Ph Me H 2-Nap C 383 (M⁺ + 1) N-f-13 NB2 N-f-3 CHO1 Ph Me Me 1Me-5-Ind C 400 (M⁺ + 1) N-f-14 NA N-f-13 Ph Me H 1Me-5-Ind C 386 (M⁺ + 1) N-f-15 NB2 N-f-5 CHO1 Ph Me Me 1Me-5-1HIdz C 401 (M⁺ + 1) N-f-16 NA N-f-15 Ph Me H 1Me-5-1HIdz C 387 (M⁺ + 1) N-f-17 NB2 Int.n-7 BRA29 4MePh H Me 2-Nap C 397 (M⁺ + 1) N-f-18 NA N-f-17 4MePh H H 2-Nap C 383 (M⁺ + 1) N-f-19 NB2 Int.n-9 BRA29 4MePh H Me 1Me-5-Ind C 400 (M⁺ + 1) N-f-20 NA N-f-19 4MePh H H 1Me-5-Ind C 386 (M⁺ + 1) N-f-21 NB2 Int.n-11 BRA29 4MePh H Me 1Me-5-1HIdz C 401 (M⁺ + 1) N-f-22 NA N-f-21 4MePh H H 1Me-51 HIdz C 387 (M⁺ + 1) N-f-23 NB2 Int.n-7 BRA60 3MePh H Me 2-Nap C 397 (M⁺ + 1) N-f-24 NA N-f-23 3MePh H H 2-Nap C 383 (M⁺ + 1) N-f-25 NB2 Int.n-9 BRA60 3MePh H Me 1Me-5-Ind C 400 (M⁺ + 1) N-f-26 NA N-f-25 3MePh H H 1Me-5-Ind C 386 (M⁺ + 1) N-f-27 NB2 Int.n-11 BRA60 3MePh H Me 1Me-5-1HIdz C 401 (M⁺ + 1) N-f-28 NA N-f-27 3MePh H H 1Me-5-1HIdz C 387 (M⁺ + 1) N-f-29 NB2 Int.n-7 BRA59 2MePh H Me 2-Nap C 397 (M⁺ + 1) N-f-30 NA N-f-29 2MePh H H 2-Nap C 383 (M⁺ + 1) N-f-31 NB2 Int.n-8 BRA59 2MePh H Me 5-Ind C 386 (M⁺ + 1) N-f-32 NA N-f-31 2MePh H H 5-Ind C 372 (M⁺ + 1) N-f-33 NB2 Int.n-10 BRA59 2MePh H Me 5-1HIdz C 387 (M⁺ + 1) N-f-34 NA N-f-33 2MePh H H 5-1HIdz C 373 (M⁺ + 1) N-f-35 NB2 Int.n-7 BRA22 4FPh H Me 2-Nap C 401 (M⁺ + 1) N-f-36 NA N-f-35 4FPh H H 2-Nap C 387 (M⁺ + 1) N-f-37 NB2 Int.n-8 BRA22 4FPh H Me 5-Ind C 390 (M⁺ + 1) N-f-38 NA N-f-37 4FPh H H 5-Ind C 376 (M⁺ + 1) N-f-39 NB2 Int.n-9 BRA22 4FPh H Me 1Me-5-Ind C 404 (M⁺ + 1) N-f-40 NA N-f-39 4FPh H H 1Me-5-Ind C 390 (M⁺ + 1) N-f-41 NB2 Int.n-7 BRA33 3FPh H Me 2-Nap C 401 (M⁺ + 1) N-f-42 NA N-f-41 3FPh H H 2-Nap C 387 (M⁺ + 1) N-f-43 NB2 Int.n-10 BRA33 3FPh H Me 5-1HIdz C 391 (M⁺ + 1) N-f-44 NA N-f-43 3FPh H H 5-1HIdz C 377 (M⁺ + 1) N-f-45 NB2 Int.n-11 BRA33 3FPh H Me 1Me-5-1HIdz C 405 (M⁺ + 1) N-f-46 NA N-f-45 3FPh H H 1Me-5-1HIdz C 391 (M⁺ + 1) N-f-47 NB2 Int.n-7 BRA32 2FPh H Me 2-Nap C 401 (M⁺ + 1) N-f-48 NA N-f-47 2FPh H H 2-Nap C 387 (M⁺ + 1) N-f-49 NB2 Int.n-8 BRA32 2FPh H Me 5-Ind C 390 (M⁺ + 1) N-f-50 NA N-f-49 2FPh H H 5-Ind C 376 (M⁺ + 1) N-f-51 NB2 Int.n-11 BRA32 2FPh H Me 1Me-5-1HIdz C 405 (M⁺ + 1) N-f-52 NA N-f-51 2FPh H H 1Me-5-1HIdz C 391 (M⁺ + 1) N-f-53 NB2 Int.n-8 BRA19 4MeOPh H Me 5-Ind C 402 (M⁺ + 1) N-f-54 NA N-f-53 4MeOPh H H 5-Ind C 388 (M⁺ + 1) N-f-55 NB2 Int.n-10 BRA19 4MeOPh H Me 5-1HIdz C 403 (M⁺ + 1) N-f-56 NA N-f-55 4MeOPh H H 5-1HIdz C 389 (M⁺ + 1) N-f-57 NB2 Int.n-11 BRA19 4MeOPh Me Me 1Me-5-1HIdz C 417 (M⁺ + 1) N-f-58 NA N-f-57 4MeOPh Me H 1Me-5-1HIdz C 403 (M⁺ + 1) N-f-59 NB2 Int.n-9 BRA37 3MeOPh Me Me 1Me-5-Ind C 416 (M⁺ + 1) N-f-60 NA N-f-59 3MeOPh Me H 1Me-5-Ind C 402 (M⁺ + 1) N-f-61 NB2 Int.n-10 BRA37 3MeOPh Me Me 5-1HIdz C 403 (M⁺ + 1) N-f-62 NA N-f-61 3MeOPh Me H 5-1HIdz C 389 (M⁺ + 1) N-f-63 NB2 Int.n-11 BRA37 3MeOPh H Me 1Me-5-1 HIdz C 417 (M⁺ + 1) N-f-64 NA N-f-63 3MeOPh H H 1Me-5-1HIdz C 403 (M⁺ + 1) N-f-65 NB2 Int.n-7 BRA38 2MeOPh H Me 2-Nap C 413 (M⁺ + 1) N-f-66 NA N-f-65 2MeOPh H H 2-Nap C 399 (M⁺ + 1) N-f-67 NB2 Int.n-8 BRA38 2MeOPh H Me 5-Ind C 402 (M⁺ + 1) N-f-68 NA N-f-67 2MeOPh H H 5-Ind C 388 (M⁺ + 1) N-f-69 NB2 Int.n-11 BRA38 2MeOPh H Me 1Me-5-1HIdz C 417 (M⁺ + 1) N-f-70 NA N-f-69 2MeOPh H H 1Me-5-1HIdz C 403 (M⁺ + 1) N-f-71 NB2 Int.n-7 BRA41 4CF3Ph H Me 2-Nap C 451 (M⁺ + 1) N-f-72 NA N-f-71 4CF3Ph H H 2-Nap C 437 (M⁺ + 1) N-f-73 NB2 Int.n-9 BRA41 4CF3Ph H Me 1Me-5-Ind C 454 (M⁺ + 1) N-f-74 NA N-f-73 4CF3Ph H H 1Me-5-Ind C 440 (M⁺ + 1) N-f-75 NB2 Int.n-11 BRA41 4CF3Ph H Me 1Me-5-1HIdz C 455 (M⁺ + 1) N-f-76 NA N-f-75 4CF3Ph H H 1Me-5-1HIdz C 441 (M⁺ + 1) N-f-77 NB2 Int.n-8 BRA88 4PhOPh H Me 5-Ind C 464 (M⁺ + 1) N-f-78 NA N-f-77 4PhOPh H H 5-Ind C 450 (M⁺ + 1) N-f-79 NB2 Int.n-9 BRA88 4PhOPh H Me 1Me-5-Ind C 478 (M⁺ + 1) N-f-80 NA N-f-79 4PhOPh H H 1Me-5-Ind C 464 (M⁺ + 1) N-f-81 NB2 Int.n-10 BRA88 4PhOPh H Me 5-1HIdz C 465 (M⁺ + 1) N-f-82 NA N-f-81 4PhOPh H H 5-1HIdz C 451 (M⁺ + 1) N-f-83 NB2 Int.n-7 BRA61 2ClPh H Me 2-Nap C 417 (M⁺ + 1) N-f-84 NA N-f-83 2ClPh H H 2-Nap C 403 (M⁺ + 1) N-f-85 NB2 Int.n-9 BRA61 2ClPh H Me 1Me-5-Ind C 420 (M⁺ + 1) N-f-86 NA N-f-85 2ClPh H H 1Me-5-Ind C 406 (M⁺ + 1) N-f-87 NB2 Int.n-10 BRA61 2ClPh H Me 5-1HIdz C 407 (M⁺ + 1) N-f-88 NA N-f-87 2ClPh H H 5-1HIdz C 393 (M⁺ + 1) N-f-89 NB2 Int.n-7 BRA73 3,5DMePh H Me 2-Nap C 411 (M⁺ + 1) N-f-90 NA N-f-89 3,5DMePh H H 2-Nap C 397 (M⁺ + 1) N-f-91 NB2 Int.n-9 BRA73 3,5DMePh H Me 1Me-5-Ind C 414 (M⁺ + 1) N-f-92 NA N-f-91 3,5DMePh H H 1Me-5-Ind C 400 (M⁺ + 1)

Example N-g-33 Synthesis of methyl 3-[4-cyclopentylamino-3-methyl-5-(naphthalen-2-yl)phenyl]propionate (Compound No. N-e-33) (Synthesis method NB1)

According to the procedure described in the synthesis method of the compound of Example N-a-1 (Synthesis method NB) provided that the reaction was carried out for 18 hours, and the column chromatography was performed with hexane:ethyl acetate=4:1), the compound of Example N-g-1 (91.6 mg), methyl boronate (140.0 mg, Ald), 2 M aqueous sodium carbonate (300 μl) and (Ph₃P)₄Pd (75.5 mg) were reacted and treated to obtain the title compound (Compound No. N-g-33, 41.3 mg).

Example N-g-251 Synthesis of methyl 3-[4-(N-methyl-N-cyclopentylamino)-3-(N-methylamino)-5-(naphthalen-2-yl)phenyl]propionate (Compound No. N-g-251) (Synthesis method NN1)

A solution of Compound No. N-g-131 (102 mg) in DMF (3 ml) was added with 60% sodium hydride (7 mg) under ice cooling, and stirred for 10 minutes. This reaction mixture was added with methyl iodide (17 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 2 hours. The reaction mixture was poured into water, and added with ethyl acetate (30 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=3:1) to obtain the title compound (Compound No. N-g-251, 30 mg).

Example N-g-285 Synthesis of methyl 3-[3-(N-dimethylamino)-4-(N-methyl-N-cyclopentylamino)-5-(naphthalen-2-yl)phenyl]propionate (Compound No. N-g-285) (Synthesis method NN2)

A solution of Compound No. N-g-131 (102 mg) in DMF (3 ml) was added with 60% sodium hydride (20 mg) under ice cooling, and stirred for 10 minutes. This reaction mixture was added dropwise with methyl iodide (100 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 16 hours. The reaction mixture was poured into water, and added with ethyl acetate (30 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 3:1) to obtain the title compound (Compound No. N-g-285, 80 mg).

Examples N-g-1 to N-g-318

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification including the examples described above are shown in Table-N-G-1 to Table-N-G-7. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-G-1

LCMS Exp. Syn SM1 SM2 Rz Ry Y Zx AR method RTime Mass N-g-1 NB1 Int.n-39 BRA1 cPen H Me Br 2-Nap C 452 (M⁺) N-g-2 NA N-g-1 cPen H H Br 2-Nap C 438 (M⁺) N-g-3 NB1 Int.n-39 BRA2 cPen H Me Br 5-Ind C 441 (M⁺) N-g-4 NA N-g-3 cPen H H Br 5-Ind C 427 (M⁺) N-g-5 NB1 Int.n-39 BRA3 cPen H Me Br 1Me-5-Ind C 455 (M⁺) N-g-6 NA N-g-5 cPen H H Br 1Me-5-Ind C 441 (M⁺) N-g-7 NB1 Int.n-39 BRA5 cPen H Me Br 5-1HIdz C 442 (M⁺) N-g-8 NA N-g-7 cPen H H Br 5-1HIdz C 428 (M⁺) N-g-9 NB1 Int.n-39 BRA6 cPen H Me Br 1Me-5-1HIdz C 456 (M⁺) N-g-10 NA N-g-9 cPen H H Br 1Me-5-1HIdz C 442 (M⁺) N-g-11 NB1 Int.n-39 BRA11 cPen H Me Br 5-Qu C 453 (M⁺) N-g-12 NA N-g-11 cPen H H Br 6-Qu C 439 (M⁺) N-g-13 NC2 N-g-1 CHO1 cPen Me Me Br 2-Nap C 466 (M⁺) N-g-14 NA N-g-13 cPen Me H Br 2-Nap C 452 (M⁺) N-g-15 NC2 N-g-5 CHO1 cPen Me Me Br 1Me-5-Ind C 455 (M⁺) N-g-16 NA N-g-15 cPen Me H Br 1Me-5-Ind C 441 (M⁺) N-g-17 NB1 Int.n-41 BRA2 nPr H Me Br 5-Ind C 415 (M⁺) N-g-18 NA N-g-17 nPr H H Br 5-Ind C 401 (M⁺) N-g-19 NB1 Int.n-41 BRA3 nPr H Me Br 1Me-5-Ind C 429 (M⁺) N-g-20 NA N-g-19 nPr H H Br 1Me-5-Ind C 415 (M⁺) N-g-21 NB1 Int.n-41 BRA5 nPr H Me Br 5-1HIdz C 416 (M⁺) N-g-22 NA N-g-21 nPr H H Br 5-1HIdz C 402 (M⁺) N-g-23 NB1 Int.n-41 BRA11 nPr H Me Br 6-Qu C 427 (M⁺) N-g-24 NA N-g-23 nPr H H Br 6-Qu C 413 (M⁺) N-g-25 NB1 Int.n-43 BRA1 iPr H Me Br 2-Nap C 426 (M⁺) N-g-26 NA N-g-25 iPr H H Br 2-Nap C 412 (M⁺) N-g-27 NB1 Int.n-43 BRA2 iPr H Me Br 5-Ind C 415 (M⁺) N-g-28 NA N-g-27 iPr H H Br 5-Ind C 401 (M⁺) N-g-29 NB1 Int.n-43 BRA6 iPr H Me Br 1Me-5-1HIdz C 430 (M⁺) N-g-30 NA N-g-29 iPr H H Br 1Me-5-1HIdz C 416 (M⁺) N-g-31 NB1 Int.n-43 BRA10 iPr H Me Br 3-Qu C 427 (M⁺) N-g-32 NA N-g-31 iPr H H Br 3-Qu C 413 (M⁺) N-g-33 NB1 N-g-1 BRA13 cPen H Me Me 2-Nap C 388 (M⁺ + 1) N-g-34 NA N-g-33 cPen H H Me 2-Nap C 374 (M⁺ + 1) N-g-35 NB1 N-g-3 BRA13 cPen H Me Me 5-Ind C 377 (M⁺ + 1) N-g-36 NA N-g-35 cPen H H Me 5-Ind C 363 (M⁺ + 1) N-g-37 NB1 N-g-5 BRA13 cPen H Me Me 1Me-5-Ind C 391 (M⁺ + 1) N-g-38 NA N-g-31 cPen H H Me 1Me-5-Ind C 377 (M⁺ + 1) N-g-39 NB1 N-g-7 BRA13 cPen H Me Me 5-1HIdz C 378 (M⁺ + 1) N-g-40 NA N-g-39 cPen H H Me 5-1HIdz C 364 (M⁺ + 1) N-g-41 NB1 N-g-9 BRA13 cPen H Me Me 1Me-5-1HIdz C 392 (M⁺ + 1) N-g-42 NA N-g-41 cPen H H Me 1Me-5-1HIdz C 378 (M⁺ + 1) N-g-43 NC2 N-g-37 CHO1 cPen Me Me Me 1Me-5-Ind C 405 (M⁺ + 1) N-g-44 NA N-g-43 cPen Me H Me 1Me-5-Ind C 391 (M⁺ + 1) N-g-45 NB1 Int.n-77 BRA1 cPen H Me NO2 2-Nap C 419 (M⁺ + 1) N-g-46 NA N-g-45 cPen H H NO2 2-Nap C 405 (M⁺ + 1) N-g-47 NB1 Int.n-77 BRA2 cPen H Me NO2 5-Ind C 408 (M⁺ + 1) N-g-48 NA N-g-47 cPen H H NO2 5-Ind C 394 (M⁺ + 1) N-g-49 NB1 Int.n-77 BRA3 cPen H Me NO2 1Me-5-Ind C 422 (M⁺ + 1) N-g-50 NA N-g-49 cPen H H NO2 1Me-5-Ind C 408 (M⁺ + 1) N-g-51 NB1 Int.n-77 BRA5 cPen H Me NO2 5-1HIdz C 409 (M⁺ + 1) N-g-52 NA N-g-51 cPen H H NO2 5-1HIdz C 395 (M⁺ + 1) N-g-53 NB1 Int.n-77 BRA6 cPen H Me NO2 1Me-5-1HIdz C 423 (M⁺ + 1) N-g-54 NA N-g-53 cPen H H NO2 1Me-5-1HIdz C 409 (M⁺ + 1) N-g-55 NB1 Int.n-78 BRA1 nPr H Me NO2 2-Nap C 393 (M⁺ + 1) N-g-56 NA N-g-55 nPr H H NO2 2-Nap C 379 (M⁺ + 1) N-g-57 NB1 Int.n-78 BRA2 nPr H Me NO2 5-Ind C 382 (M⁺ + 1) N-g-58 NA N-g-57 nPr H H NO2 5-Ind C 358 (M⁺ + 1) N-g-59 NB1 Int.n-78 BRA3 nPr H Me NO2 1Me-5-Ind C 396 (M⁺ + 1) N-g-60 NA N-g-59 nPr H H NO2 1Me-5-Ind C 382 (M⁺ + 1) N-g-61 NB1 Int.n-78 BRA5 nPr H Me NO2 5-1HIdz C 383 (M⁺ + 1) N-g-62 NA N-g-61 nPr H H NO2 5-1HIdz C 369 (M⁺ + 1) N-g-63 NB1 Int.n-78 BRA6 nPr H Me NO2 1Me-5-1HIdz C 397 (M⁺ + 1) N-g-64 NA N-g-63 nPr H H NO2 1Me-5-1HIdz C 383 (M⁺ + 1) N-g-65 NB1 Int.n-79 BRA1 iPr H Me NO2 2-Nap C 393 (M⁺ + 1) N-g-66 NA N-g-65 iPr H H NO2 2-Nap C 379 (M⁺ + 1) N-g-67 NB1 Int.n-79 BRA2 iPr H Me NO2 5-Ind C 382 (M⁺ + 1) N-g-68 NA N-g-67 iPr H H NO2 5-Ind C 368 (M⁺ + 1) N-g-69 NB1 Int.n-79 BRA3 iPr H Me NO2 1Me-5-Ind C 396 (M⁺ + 1) N-g-70 NA N-g-69 iPr H H NO2 1Me-5-Ind C 382 (M⁺ + 1) N-g-71 NB1 Int.n-79 BRA5 iPr H Me NO2 5-1HIdz C 383 (M⁺ + 1) N-g-72 NA N-g-71 iPr H H NO2 5-1HIdz C 369 (M⁺ + 1) N-g-73 NB1 Int.n-79 BRA6 iPr H Me NO2 1Me-5-1HIdz C 397 (M⁺ + 1) N-g-74 NA N-g-73 iPr H H NO2 1Me-5-1HIdz C 383 (M⁺ + 1) N-g-75 NB1 Int.n-83 BRA1 cPen Me Me NO2 2-Nap C 433 (M⁺ + 1) N-g-76 NA N-g-75 cPen Me H NO2 2-Nap C 419 (M⁺ + 1) N-g-77 NB1 Int.n-83 BRA3 cPen Me Me NO2 1Me-5-Ind C 436 (M⁺ + 1) N-g-78 NA N-g-77 cPen Me H NO2 1Me-5-Ind C 422 (M⁺ + 1) N-g-79 NB1 Int.n-83 BRA6 cPen Me Me NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-g-80 NA N-g-79 cPen Me H NO2 1Me-5-IHIdz C 423 (M⁺ + 1) N-g-81 NB1 Int.n-84 BRA1 nPr Me Me NO2 2-Nap C 407 (M⁺ + 1) N-g-82 NA N-g-81 nPr Me H NO2 2-Nap C 393 (M⁺ + 1) N-g-83 NB1 Int.n-84 BRA2 nPr Me Me NO2 5-Ind C 396 (M⁺ + 1) N-g-84 NA N-g-83 nPr Me H NO2 5-Ind C 382 (M⁺ + 1) N-g-85 NB1 Int.n-84 BRA3 nPr Me Me NO2 1Me-5-Ind C 410 (M⁺ + 1) N-g-86 NA N-g-85 nPr Me H NO2 1Me-5-Ind C 396 (M⁺ + 1) N-g-87 NB1 Int.n-84 BRA5 nPr Me Me NO2 5-1HIdz C 397 (M⁺ + 1) N-g-88 NA N-g-87 nPr Me H NO2 5-1HIdz C 383 (M⁺ + 1) N-g-89 NB Int.n-84 BRA6 nPr Me Me NO2 1Me-5-1HIdz C 411 (M⁺ + 1) N-g-90 NA N-g-89 nPr Me H NO2 1Me-5-1HIdz C 397 (M⁺ + 1) N-g-91 NB1 Int.n-85 BRA1 iPr Me Me NO2 2-Nap C 407 (M⁺ + 1) N-g-92 NA N-g-91 iPr Me H NO2 2-Nap C 393 (M⁺ + 1) N-g-93 NB1 Int.n-85 BRA2 iPr Me Me NO2 5-Ind C 396 (M⁺ + 1) N-g-94 NA N-g-93 iPr Me H NO2 5-Ind C 382 (M⁺ + 1) N-g-95 NB1 Int.n-85 BRA3 iPr Me Me NO2 1Me-5-Ind C 410 (M⁺ + 1) N-g-96 NA N-g-95 iPr Me H NO2 1Me-5-Ind C 396 (M⁺ + 1) N-g-97 NB1 Int.n-85 BRA5 iPr Me Me NO2 5-1HIdz C 397 (M⁺ + 1) N-g-98 NA N-g-97 iPr Me H NO2 5-1HIdz C 383 (M⁺ + 1) N-g-99 NB1 Int.n-85 BRA6 iPr Me Me NO2 1Me-5-1HIdz C 411 (M⁺ + 1) N-g-100 NA N-g-99 iPr Me H NO2 1Me-5-1HIdz C 397 (M⁺ + 1) N-g-101 ND1 N-g-45 cPen H Me NH2 2-Nap C 389 (M⁺ + 1) N-g-102 NA N-g-101 cPen H H NH2 2-Nap C 375 (M⁺ + 1) N-g-103 ND1 N-g-47 cPen H Me NH2 5-Ind C 378 (M⁺ + 1) N-g-104 NA N-g-103 cPen H H NH2 5-Ind C 364 (M⁺ + 1) N-g-105 ND1 N-g-49 cPen H Me NH2 1Me-5-Ind C 392 (M⁺ + 1) N-g-106 NA N-g-105 cPen H H NH2 1Me-5-Ind C 378 (M⁺ + 1) N-g-107 ND1 N-g-51 cPen H Me NH2 5-1HIdz C 379 (M⁺ + 1) N-g-108 NA N-g-107 cPen H H NH2 5-1HIdz C 365 (M⁺ + 1) N-g-109 ND1 N-g-53 cPen H Me NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-g-110 NA N-g-109 cPen H H NH2 1Me-5-1HIdz C 379 (M⁺ + 1) N-g-111 ND1 N-g-55 nPr H Me NH2 2-Nap C 363 (M⁺ + 1) N-g-112 NA N-g-111 nPr H H NH2 2-Nap C 349 (M⁺ + 1) N-g-113 ND1 N-g-57 nPr H Me NH2 5-Ind C 352 (M⁺ + 1) N-g-114 NA N-g-113 nPr H H NH2 5-Ind C 338 (M⁺ + 1) N-g-115 ND1 N-g-59 nPr H Me NH2 1Me-5-Ind C 366 (M⁺ + 1) N-g-116 NA N-g-115 nPr H H NH2 1Me-5-Ind C 352 (M⁺ + 1) N-g-117 ND1 N-g-61 nPr H Me NH2 5-1HIdz C 353 (M⁺ + 1) N-g-118 NA N-g-117 nPr H H NH2 5-1HIdz C 339 (M⁺ + 1) N-g-119 ND1 N-g-63 nPr H Me NH2 1Me-5-1HIdz C 367 (M⁺ + 1) N-g-120 NA N-g-119 nPr H H NH2 1Me-5-1HIdz C 353 (M⁺ + 1) N-g-121 ND1 N-g-65 iPr H Me NH2 2-Nap C 363 (M⁺ + 1) N-g-122 NA N-g-121 iPr H H NH2 2-Nap C 349 (M⁺ + 1) N-g-123 ND1 N-g-67 iPr H Me NH2 5-Ind C 352 (M⁺ + 1) N-g-124 NA N-g-123 iPr H H NH2 5-Ind C 338 (M⁺ + 1) N-g-125 ND1 N-g-69 iPr H Me NH2 1Me-5-Ind C 366 (M⁺ + 1) N-g-126 NA N-g-125 iPr H H NH2 1Me-5-Ind C 352 (M⁺ + 1) N-g-127 ND1 N-g-71 iPr H Me NH2 5-1HIdz C 353 (M⁺ + 1) N-g-128 NA N-g-127 iPr H H NH2 5-1HIdz C 339 (M⁺ + 1) N-g-129 ND1 N-g-73 iPr H Me NH2 1Me-5-1HIdz C 367 (M⁺ + 1) N-g-130 NA N-g-129 iPr H H NH2 1Me-5-1HIdz C 353 (M⁺ + 1) N-g-131 NC1 N-g-75 cPen Me Me NH2 2-Nap C 389 (M⁺ + 1) N-g-132 NA N-g-131 cPen Me H NH2 2-Nap C 375 (M⁺ + 1) N-g-133 NC1 N-g-77 cPen Me Me NH2 1Me-5-Ind C 392 (M⁺ + 1) N-g-134 NA N-g-133 cPen Me H NH2 1Me-5-Ind C 378 (M⁺ + 1) N-g-135 NC1 N-g-79 cPen Me Me NH2 5-1HIdz C 379 (M⁺ + 1) N-g-136 NA N-g-135 cPen Me H NH2 5-1HIdz C 365 (M⁺ + 1) N-g-137 NC1 N-g-81 cPen Me Me NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-g-138 NA N-g-137 cPen Me H NH2 1Me-5-1HIdz C 379 (M⁺ + 1) N-g-139 ND1 N-g-83 nPr Me Me NH2 2-Nap C 363 (M⁺ + 1) N-g-140 NA N-g-139 nPr Me H NH2 2-Nap C 349 (M⁺ + 1) N-g-141 ND1 N-g-85 nPr Me Me NH2 5-Ind C 352 (M⁺ + 1) N-g-142 NA N-g-141 nPr Me H NH2 5-Ind C 338 (M⁺ + 1) N-g-143 ND1 N-g-87 nPr Me Me NH2 1Me-5-Ind C 366 (M⁺ + 1) N-g-144 NA N-g-143 nPr Me H NH2 1Me-5-Ind C 352 (M⁺ + 1) N-g-145 ND1 N-g-89 nPr Me Me NH2 5-1HIdz C 353 (M⁺ + 1) N-g-146 NA N-g-145 nPr Me H NH2 5-1HIdz C 339 (M⁺ + 1) N-g-147 ND1 N-g-91 nPr Me Me NH2 1Me-5-1HIdz C 367 (M⁺ + 1) N-g-148 NA N-g-147 nPr Me H NH2 1Me-5-1HIdz C 353 (M⁺ + 1) N-g-149 ND1 N-g-93 iPr Me Me NH2 2-Nap C 363 (M⁺ + 1) N-g-150 NA N-g-149 iPr Me H NH2 2-Nap C 349 (M⁺ + 1) N-g-151 ND1 N-g-95 iPr Me Me NH2 1Me-5-Ind C 366 (M⁺ + 1) N-g-152 NA N-g-151 iPr Me H NH2 1Me-5-Ind C 352 (M⁺ + 1) N-g-153 ND1 N-g-97 iPr Me Me NH2 5-1HIdz C 353 (M⁺ + 1) N-g-154 NA N-g-153 iPr Me H NH2 5-1HIdz C 339 (M⁺ + 1) N-g-155 ND1 N-g-99 iPr Me Me NH2 1Me-5-1HIdz C 367 (M⁺ + 1) N-g-156 NA N-g-155 iPr Me H NH2 1Me-5-1HIdz C 353 (M⁺ + 1) N-g-157 NB1 Int.n-80 BRA1 2-Indane H Me NO2 2-Nap C 467 (M⁺ + 1) N-g-158 NA N-g-157 2-Indane H H NO2 2-Nap C 453 (M⁺ + 1) N-g-159 NB1 Int.n-80 BRA2 2-Indane H Me NO2 5-Ind C 456 (M⁺ + 1) N-g-160 NA N-g-159 2-Indane H H NO2 5-Ind C 442 (M⁺ + 1) N-g-161 NB1 Int.n-80 BRA3 2-Indane H Me NO2 1Me-5-Ind C 470 (M⁺ + 1) N-g-162 NA N-g-161 2-Indane H H NO2 1Me-5-Ind C 456 (M⁺ + 1) N-g-163 NB1 Intn80 BRA5 2-Indane H Me NO2 5-1HIdz C 457 (M⁺ + 1) N-g-164 NA N-g-163 2-Indane H H NO2 5-1HIdz C 443 (M⁺ + 1) N-g-165 NB1 Int.n-80 BRA5 2-Indane H Me NO2 1Me-5-1HIdz C 471 (M⁺ + 1) N-g-166 NA N-g-165 2-Indane H H NO2 1Me-5-1HIdz C 457 (M⁺ + 1) N-g-167 NB1 Int.n-81 BRA2 cHex H Me NO2 5-Ind C 422 (M⁺ + 1) N-g-168 NA N-g-167 cHex H H NO2 5-Ind C 408 (M⁺ + 1) N-g-169 NB1 Int.n-81 BRA3 cHex H Me NO2 1Me-5-Ind C 436 (M⁺ + 1) N-g-170 NA N-g-169 cHex H H NO2 1Me-5-Ind C 422 (M⁺ + 1) N-g-171 NB1 Int.n-81 BRA5 cHex H Me NO2 5-1HIdz C 423 (M⁺ + 1) N-g-172 NA N-g-171 cHex H H NO2 5-1HIdz C 409 (M⁺ + 1) N-g-173 NB1 Int.n-81 BRA5 cHex H Me NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-g-174 NA N-g-173 cHex H H NO2 1Me-5-1HIdz C 423 (M⁺ + 1) N-g-175 NB1 Int.n-82 BRA1 2(Me)cHex H Me NO2 2-Nap C 447 (M⁺ + 1) N-g-176 NA N-g-175 2(Me)cHex H H NO2 2-Nap C 433 (M⁺ + 1) N-g-177 NB1 Int.n-82 BRA2 2(Me)cHex H Me NO2 5-Ind C 436 (M⁺ + 1) N-g-178 NA N-g-177 2(Me)cHex H H NO2 5-Ind C 422 (M⁺ + 1) N-g-179 NB1 Int.n-82 BRA3 2(Me)cHex H Me NO2 IMe-5-Ind C 450 (M⁺ + 1) N-g-180 NA N-g-179 2(Me)cHex H H NO2 1Me-5-Ind C 436 (M⁺ + 1) N-g-181 NB1 Int.n-82 BRA5 2(Me)cHex H Me NO2 5-1HIdz C 437 (M⁺ + 1) N-g-182 NA N-g-181 2(Me)cHex H H NO2 5-1HIdz C 423 (M⁺ + 1) N-g-183 NB1 Int.n-82 BRA5 2(Me)cHex H Me NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-g-184 NA N-g-183 2(Me)cHex H H NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-g-185 NB1 Int.n-86 BRA1 2-Indane Me Me NO2 2-Nap C 481 (M⁺ + 1) N-g-186 NA N-g-185 2-Indane Me H NO2 2-Nap C 467 (M⁺ + 1) N-g-187 NB1 Int.n-86 BRA3 2-Indane Me Me NO2 1Me-5-Ind C 484 (M⁺ + 1) N-g-188 NA N-g-187 2-Indane Me H NO2 1Me-5-Ind C 470 (M⁺ + 1) N-g-189 NB1 Int.n-86 BRA5 2-Indane Me Me NO2 5-1HIdz C 471 (M⁺ + 1) N-g-190 NA N-g-189 2-Indane Me H NO2 5-1HIdz C 457 (M⁺ + 1) N-g-191 NB1 Int.n-86 BRA6 2-Indane Me Me NO2 1Me-5-1HIdz C 485 (M⁺ + 1) N-g-192 NA N-g-191 2-Indane Me H NO2 1Me-5-1HIdz C 471 (M⁺ + 1) N-g-193 NB1 Int.n-87 BRA1 cHex Me Me NO2 2-Nap C 447 (M⁺ + 1) N-g-194 NA N-g-193 cHex Me H NO2 2-Nap C 433 (M⁺ + 1) N-g-195 NB1 Int.n-87 BRA3 cHex Me Me NO2 1Me-5-Ind C 450 (M⁺ + 1) N-g-198 NA N-g-195 cHex Me H NO2 1Me-5-Ind C 436 (M⁺ + 1) N-g-197 NB1 Int.n-87 BRA5 cHex Me Me NO2 5-1HIdz C 437 (M⁺ + 1) N-g-198 NA N-g-197 cHex Me H NO2 5-1HIdz C 423 (M⁺ + 1) N-g-199 NB1 Int.n-87 BRA6 cHex Me Me NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-g-200 NA N-g-199 cHex Me H NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-g-201 NB1 Int.n-88 BRA1 4(Me)cHex Me Me NO2 2-Nap C 461 (M⁺ + 1) N-g-202 NA N-g-201 4(Me)cHex Me H NO2 2-Nap C 447 (M⁺ + 1) N-g-203 NB1 Int.n-88 BRA3 4(Me)cHex Me Me NO2 1Me-5-Ind C 464 (M⁺ + 1) N-g-204 NA N-g-203 4(Me)cHex Me H NO2 1Me-5-Ind C 450 (M⁺ + 1) N-g-205 NB1 Int.n-88 BRA6 4(Me)cHex Me Me NO2 1Me-5-1HIdz C 465 (M⁺ + 1) N-g-206 NA N-g-205 4(Me)cHex Me H NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-g-207 ND1 N-g-159 2-Indane H Me NH2 5-Ind C 426 (M⁺ + 1) N-g-208 NA N-g-207 2-Indane H H NH2 5-Ind C 412 (M⁺ + 1) N-g-209 ND1 N-g-161 2-Indane H Me NH2 1Me-5-Ind C 440 (M⁺ + 1) N-g-210 NA N-g-209 2-Indane H H NH2 1Me-5-Ind C 426 (M⁺ + 1) N-g-211 ND1 N-g-163 2-Indane H Me NH2 5-1HIdz C 427 (M⁺ + 1) N-g-212 NA N-g-211 2-Indane H H NH2 5-1HIdz C 413 (M⁺ + 1) N-g-213 ND1 N-g-165 2-Indane H Me NH2 1Me-5-1HIdz C 441 (M⁺ + 1) N-g-214 NA N-g-213 2-Indane H H NH2 1Me-5-1HIdz C 427 (M⁺ + 1) N-g-215 ND1 N-g-167 cHex H Me NH2 5-Ind C 392 (M⁺ + 1) N-g-216 NA N-g-215 cHex H H NH2 5-Ind C 378 (M⁺ + 1) N-g-217 ND1 N-g-169 cHex H Me NH2 1Me-5-Ind C 406 (M⁺ + 1) N-g-218 NA N-g-217 cHex H H NH2 1Me-5-Ind C 392 (M⁺ + 1) N-g-219 ND1 N-g-171 cHex H Me NH2 5-1HIdz C 393 (M⁺ + 1) N-g-220 NA N-g-219 cHex H H NH2 5-1HIdz C 379 (M⁺ + 1) N-g-221 ND1 N-g-173 cHex H Me NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-g-222 NA N-g-221 cHex H H NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-g-223 ND1 N-g-177 4(Me)cHex H Me NH2 5-Ind C 406 (M⁺ + 1) N-g-224 NA N-g-223 4(Me)cHex H H NH2 5-Ind C 392 (M⁺ + 1) N-g-225 ND1 N-g-179 4(Me)cHex H Me NH2 1Me-5-Ind C 420 (M⁺ + 1) N-g-226 NA N-g-225 4(Me)cHex H H NH2 1Me-5-Ind C 406 (M⁺ + 1) N-g-227 ND1 N-g-181 4(Me)cHex H Me NH2 5-1HIdz C 407 (M⁺ + 1) N-g-228 NA N-g-227 4(Me)cHex H H NH2 5-1HIdz C 393 (M⁺ + 1) N-g-229 ND1 N-g-183 4(Me)cHex H Me NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-g-230 NA N-g-229 4(Me)cHex H H NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-g-231 ND1 N-g-185 2-Indane Me Me NH2 2-Nap C 451 (M⁺ + 1) N-g-232 NA N-g-231 2-Indane Me H NH2 2-Nap C 437 (M⁺ + 1) N-g-233 ND1 N-g-187 2-Indane Me Me NH2 1Me-5-Ind C 454 (M⁺ + 1) N-g-234 NA N-g-233 2-Indane Me H NH2 1 Me-5-Ind C 440 (M⁺ + 1) N-g-235 ND1 N-g-191 2-Indane Me Me NH2 1Me-5-1HIdz C 455 (M⁺ + 1) N-g-236 NA N-g-235 2-Indane Me H NH2 1Me-5-1HIdz C 441 (M⁺ + 1) N-g-237 ND1 N-g-193 cHex Me Me NH2 2-Nap C 417 (M⁺ + 1) N-g-238 NA N-g-237 cHex Me H NH2 2-Nap C 403 (M⁺ + 1) N-g-239 ND1 N-g-195 cHex Me Me NH2 1Me-5-Ind C 420 (M⁺ + 1) N-g-240 NA N-g-239 cHex Me H NH2 1Me-5-Ind C 406 (M⁺ + 1) N-g-241 ND1 N-g-197 cHex Me Me NH2 5-1HIdz C 407 (M⁺ + 1) N-g-242 NA N-g-241 cHex Me H NH2 5-1HIdz C 393 (M⁺ + 1) N-g-243 ND1 N-g-199 cHex Me Me NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-g-244 NA N-g-243 cHex Me H NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-g-245 ND1 N-g-201 4(Me)cHex Me Me NH2 2-Nap C 431 (M⁺ + 1) N-g-246 NA N-g-245 4(Me)cHex Me H NH2 2-Nap C 417 (M⁺ + 1) N-g-247 ND1 N-g-203 4(Me)cHex Me Me NH2 1Me-5-Ind C 434 (M⁺ + 1) N-g-248 NA N-g-247 4(Me)cHex Me H NH2 1 Me-5-Ind C 420 (M⁺ + 1) N-g-249 ND1 N-g-205 4(Me)cHex Me Me NH2 1Me-5-1HIdz C 435 (M⁺ + 1) N-g-250 NA N-g-249 4(Me)cHex Me H NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-g-251 NN1 N-g-131 CH₃I cPen Me Me NHMe 2-Nap C 417 (M⁺ + 1) N-g-252 NA N-g-251 cPen Me H NHMe 2-Nap C 403 (M⁺ + 1) N-g-253 NN1 N-g-133 CH₃I cPen Me Me NHMe 1Me-5-Ind C 420 (M⁺ + 1) N-g-254 NA N-g-253 cPen Me H NHMe 1Me-5-Ind C 406 (M⁺ + 1) N-g-255 NN1 N-g-137 CH₃I cPen Me Me NHMe 1Me-5-1HIdz C 421 (M⁺ + 1) N-g-256 NA N-g-255 cPen Me H NHMe 1Me-5-1HIdz C 407 (M⁺ + 1) N-g-257 NN1 N-g-139 CH₃I nPr Me Me NHMe 2-Nap C 391 (M⁺ + 1) N-g-258 NA N-g-257 nPr Me H NHMe 2-Nap C 377 (M⁺ + 1) N-g-259 NN1 N-g-143 CH₃I nPr Me Me NHMe 1Me-5-Ind C 394 (M⁺ + 1) N-g-260 NA N-g-259 nPr Me H NHMe 1Me-5-Ind C 380 (M⁺ + 1) N-g-261 NN1 N-g-147 CH₃I nPr Me Me NHMe 1Me-5-1HIdz C 395 (M⁺ + 1) N-g-262 NA N-g-261 nPr Me H NHMe 1Me-5-1HIdz C 381 (M⁺ + 1) N-g-263 NN1 N-g-149 CH₃I iPr Me Me NHMe 2-Nap C 391 (M⁺ + 1) N-g-264 NA N-g-263 iPr Me H NHMe 2-Nap C 377 (M⁺ + 1) N-g-265 NN1 N-g-151 CH₃I iPr Me Me NHMe 1Me-5-Ind C 394 (M⁺ + 1) N-g-266 NA N-g-265 iPr Me H NHMe 1Me-5-Ind C 380 (M⁺ + 1) N-g-267 NN1 N-g-155 CH₃I iPr Me Me NHMe 1Me-5-1HIdz C 395 (M⁺ + 1) N-g-268 NA N-g-267 iPr Me H NHMe 1Me-5-1HIdz C 381 (M⁺ + 1) N-g-269 NN1 N-g-231 CH₃I 2-Indane Me Me NHMe 2-Nap C 465 (M⁺ + 1) N-g-270 NA N-g-269 2-Indane Me H NHMe 2-Nap C 451 (M⁺ + 1) N-g-271 NN1 N-g-233 CH₃I 2-Indane Me Me NHMe 1Me-5-Ind C 468 (M⁺ + 1) N-g-272 NA N-g-271 2-Indane Me H NHMe 1Me-5-Ind C 454 (M⁺ + 1) N-g-273 NN1 N-g-235 CH₃I 2-Indane Me Me NHMe 1Me-5-1HIdz C 469 (M⁺ + 1) N-g-274 NA N-g-273 2-Indane Me H NHMe 1Me-5-1HIdz C 455 (M⁺+ 1) N-g-275 NN1 N-g-237 CH₃I cHex Me Me NHMe 2-Nap C 431 (M⁺ + 1) N-g-276 NA N-g-275 cHex Me H NHMe 2-Nap C 417 (M⁺ + 1) N-g-277 NN1 N-g-239 CH₃I cHex Me Me NHMe 1Me-5-Ind C 434 (M⁺ + 1) N-g-278 NA N-g-277 cHex Me H NHMe 1Me-5-Ind C 420 (M⁺ + 1) N-g-279 NN1 N-g-245 CH₃I 4Me-cHex Me Me NHMe 2-Nap C 445 (M⁺ + 1) N-g-280 NA N-g-279 4Me-cHex Me H NHMe 2-Nap C 431 (M⁺ + 1) N-g-281 NN2 N-g-247 CH₃I 4Me-cHex Me Me NMe₂ 1Me-5-Ind C 448 (M⁺ + 1) N-g-282 NA N-g-281 4Me-cHex Me H NMe₂ 1Me-5-Ind C 434 (M⁺ + 1) N-g-283 NN2 N-g-249 CH₃I 4Me-cHex Me Me NMe₂ 1Me-5-1HIdz C 449 (M⁺ + 1) N-g-284 NA N-g-283 4Me-cHex Me H NMe₂ 1Me-5-1 HIdz C 435 (M⁺ + 1) N-g-285 NN2 N-g-131 CH₃I cPen Me Me NMe₂ 2-Nap C 431 (M⁺ + 1) N-g-286 NA N-g-285 cPen Me H NMe₂ 2-Nap C 417 (M⁺ + 1) N-g-287 NN2 N-g-133 CH₃I cPen Me Me NMe₂ 1Me-5-Ind C 434 (M⁺ + 1) N-g-288 NA N-g-287 cPen Me H NMe₂ 1Me-5-Ind C 420 (M⁺ + 1) N-g-289 NN2 N-g-137 CH₃I cPen Me Me NMe₂ 1Me-5-1HIdz C 435 (M⁺ + 1) N-g-290 NA N-g-289 cPen Me H NMe₂ 1Me-5-1HIdz C 421 (M⁺ + 1) N-g-291 NN2 N-g-139 CH₃I nPr Me Me NMe₂ 2-Nap C 405 (M⁺ + 1) N-g-292 NA N-g-291 nPr Me H NMe₂ 2-Nap C 391 (M⁺ + 1) N-g-293 NN2 N-g-143 CH₃I nPr Me Me NMe₂ 1Me-5-Ind C 408 (M⁺ + 1) N-g-294 NA N-g-293 nPr Me H NMe₂ 1Me-5-Ind C 394 (M⁺ + 1) N-g-295 NN2 N-g-147 CH₃I nPr Me Me NMe₂ 1Me-5-1HIdz C 409 (M⁺ + 1) N-g-296 NA N-g-295 nPr Me H NMe₂ 1Me-5-1HIdz C 395 (M⁺ + 1) N-g-297 NN2 N-g-149 CH₃I iPr Me Me NMe₂ 2-Nap C 405 (M⁺ + 1) N-g-298 NA N-g-297 iPr Me H NMe₂ 2-Nap C 391 (M⁺ + 1) N-g-299 NN2 N-g-151 CH₃I iPr Me Me NMe₂ 1Me-5-Ind C 408 (M⁺ + 1) N-g-300 NA N-g-299 iPr Me H NMe₂ 1Me-5-Ind C 394 (M⁺ + 1) N-g-301 NN2 N-g-155 CH₃I iPr Me Me NMe₂ 1Me-5-1HIdz C 409 (M⁺ + 1) N-g-302 NA N-g-301 iPr Me H NMe₂ 1Me-5-1HIdz C 395 (M⁺ + 1) N-g-303 NN2 N-g-231 CH₃I 2-Indane Me Me NMe₂ 2-Nap C 479 (M⁺ + 1) N-g-304 NA N-g-303 2-Indane Me H NMe₂ 2-Nap C 465 (M⁺ + 1) N-g-305 NN2 N-g-233 CH₃I 2-Indane Me Me NMe₂ 1Me-5-Ind C 482 (M⁺ + 1) N-g-306 NA N-g-305 2-Indane Me H NMe₂ 1Me-5-Ind C 468 (M⁺ + 1) N-g-307 NN2 N-g-235 CH₃I 2-Indane Me Me NMe₂ 1Me-5-1HIdz C 483 (M⁺ + 1) N-g-308 NA N-g-307 2-Indane Me H NMe₂ 1Me-5-1HIdz C 469 (M⁺ + 1) N-g-309 NN2 N-g-237 CH₃I cHex Me Me NMe₂ 2-Nap C 445 (M⁺ + 1) N-g-310 NA N-g-265 cHex Me H NMe₂ 2-Nap C 431 (M⁺ + 1) N-g-311 NN2 N-g-239 CH₃I cHex Me Me NMe₂ 1Me-5-Ind C 448 (M⁺ + 1) N-g-312 NA N-g-267 cHex Me H NMe₂ 1Me-5-Ind C 434 (M⁺ + 1) N-g-313 NN2 N-g-245 CH₃I 4Me-cHex Me Me NMe₂ 2-Nap C 459 (M⁺ + 1) N-g-314 NA N-g-269 4Me-cHex Me H NMe₂ 2-Nap C 445 (M⁺ + 1) N-g-315 NN2 N-g-247 CH₃I 4Me-cHex Me Me NMe₂ 1Me-5-Ind C 462 (M⁺ + 1) N-g-316 NA N-g-271 4Me-cHex Me H NMe₂ 1Me-5-Ind C 448 (M⁺ + 1) N-g-317 NN2 N-g-249 CH₃I 4Me-cHex Me Me NMe₂ 1Me-5-1HIdz C 463 (M⁺ + 1) N-g-318 NA N-g-273 4Me-cHex Me H NMe₂ 1Me-5-1HIdz C 449 (M⁺ + 1)

Examples N-h-1 to N-h-458

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-N-H-1 to Table-N-H-10. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, corresponding methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-H-1

LCMS Exp. Syn SM1 SM2 Rz Ry Y Zx AR method RTime Mass N-h-1 NB1 Int.n-89 BRA1 Bn H Me NO2 2-Nap C 441 (M⁺ + 1) N-h-2 NA N-h-1 Bn H H NO2 2-Nap C 427 (M⁺ + 1) N-h-3 NB1 Int.n-89 BRA2 Bn H Me NO2 5-Ind C 430 (M⁺ + 1) N-h-4 NA N-h-3 Bn H H NO2 5-Ind C 416 (M⁺ + 1) N-h-5 NB1 Int.n-89 BRA3 Bn H Me NO2 1Me-5-Ind C 444 (M⁺ + 1) N-h-6 NA N-h-5 Bn H H NO2 1Me-5-Ind C 430 (M⁺ + 1) N-h-7 NB1 Int.n-89 BRA5 Bn H Me NO2 5-1HIdz C 431 (M⁺ + 1) N-h-8 NA N-h-1 Bn H H NO2 5-1HIdz C 417 (M⁺ + 1) N-h-9 NB1 Int.n-89 BRA6 Bn H Me NO2 1Me-5-1HIdz C 445 (M⁺ + 1) N-h-10 NA N-h-9 Bn H H NO2 1Me-5-1HIdz C 431 (M⁺ + 1) N-h-11 NB1 Int.n-89 BRA10 Bn H Me NO2 3-Qu C 442 (M⁺ + 1) N-h-12 NA N-h-11 Bn H H NO2 3-Qu C 428 (M⁺ + 1) N-h-13 NB1 Int.n-89 BRA11 Bn H Me NO2 6-Qu C 442 (M⁺ + 1) N-h-14 NA N-h-13 Bn H H NO2 6-Qu C 428 (M⁺ + 1) N-h-15 NB1 Int.n-89 BRA12 Bn H Me NO2 6-IQ C 442 (M⁺ + 1) N-h-16 NA N-h-15 Bn H H NO2 6-IQ C 428 (M⁺ + 1) N-h-17 NB1 Int.n-90 BRA1 4FBn H Me NO2 2-Nap C 459 (M⁺ + 1) N-h-18 NA N-h-17 4FBn H H NO2 2-Nap C 445 (M⁺ + 1) N-h-19 NB1 Int.n-90 BRA2 4FBn H Me NO2 5-Ind C 448 (M⁺ + 1) N-h-20 NA N-h-19 4FBn H H NO2 5-Ind C 434 (M⁺ + 1) N-h-21 NB1 Int.n-90 BRA3 4FBn H Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-22 NA N-h-21 4FBn H H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-23 NB1 Int.n-90 BRA5 4FBn H Me NO2 5-1HIdz C 449 (M⁺ + 1) N-h-24 NA N-h-23 4FBn H H NO2 5-1HIdz C 435 (M⁺ + 1) N-h-25 NB1 Int.n-90 BRA6 4FBn H Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-26 NA N-h-25 4FBn H H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-27 NB1 Int.n-91 BRA2 2FBn H Me NO2 5-Ind C 448 (M⁺ + 1) N-h-28 NA N-h-27 2FBn H H NO2 5-Ind C 434 (M⁺ + 1) N-h-29 NB1 Int.n-91 BRA3 2FBn H Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-30 NA N-h-29 2FBn H H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-31 NB1 Int.n-91 BRA5 2FBn H Me NO2 5-1HIdz C 449 (M⁺ + 1) N-h-32 NA N-h-31 2FBn H H NO2 5-1HIdz C 435 (M⁺ + 1) N-h-33 NB1 Int.n-91 BRA6 2FBn H Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-34 NA N-h-33 2FBn H H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-35 NB1 Int.n-92 BRA2 3FBn H Me NO2 5-Ind C 448 (M⁺ + 1) N-h-36 NA N-h-35 3FBn H H NO2 5-Ind C 434 (M⁺ + 1) N-h-37 NB1 Int.n-92 BRA3 3FBn H Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-38 NA N-h-37 3FBn H H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-39 NB1 Int.n-92 BRA5 3FBn H Me NO2 5-1Hldz C 449 (M⁺ + 1) N-h-40 NA N-h-39 3FBn H H NO2 5-1Hldz C 435 (M⁺ + 1) N-h-41 NB1 Int.n-92 BRA6 3FBn H Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-42 NA N-h-41 3FBn H H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-43 NB1 Int.n-93 BRA1 2,3DFBn H Me NO2 2-Nap C 477 (M⁺ + 1) N-h-44 NA N-h-43 2,3DFBn H H NO2 2-Nap C 463 (M⁺ + 1) N-h-45 NB1 Int.n-93 BRA3 2,3DFBn H Me NO2 1Me-5-Ind C 480 (M⁺ + 1) N-h-46 NA N-h-45 2,3DFBn H H NO2 1Me-5-Ind C 466 (M⁺ + 1) N-h-47 NB1 Int.n-93 BRA5 2,3DFBn H Me NO2 5-1HIdz C 467 (M⁺ + 1) N-h-48 NA N-h-47 2,3DFBn H H NO2 5-1HIdz C 453 (M⁺ + 1) N-h-49 NB1 Int.n-93 BRA6 2,3DFBn H Me NO2 1Me-5-1HIdz C 481 (M⁺ + 1) N-h-50 NA N-h-49 2,3DFBn H H NO2 1Me-5-1HIdz C 467 (M⁺ + 1) N-h-51 NB1 Int.n-94 BRA2 3,4DFBn H Me NO2 5-Ind C 466 (M⁺ + 1) N-h-52 NA N-h-51 3,4DFBn H H NO2 5-Ind C 452 (M⁺ + 1) N-h-53 NB1 Int.n-94 BRA3 3,4DFBn H Me NO2 1Me-5-Ind C 480 (M⁺ + 1) N-h-54 NA N-h-53 3,4DFBn H H NO2 1Me-5-Ind C 466 (M⁺ + 1) N-h-55 NB1 Int.n-94 BRA6 3,4DFBn H Me NO2 1Me-5-1HIdz C 481 (M⁺ + 1) N-h-56 NA N-h-55 3,4DFBn H H NO2 1Me-5-1HIdz C 467 (M⁺ + 1) N-h-57 NB1 Int.n-95 BRA1 4PhBn H Me NO2 2-Nap C 517 (M⁺ + 1) N-h-58 NA N-h-57 4PhBn H H NO2 2-Nap C 503 (M⁺ + 1) N-h-59 NB1 Int.n-95 BRA2 4PhBn H Me NO2 5-Ind C 506 (M⁺ + 1) N-h-60 NA N-h-59 4PhBn H H NO2 5-Ind C 492 (M⁺ + 1) N-h-61 NB1 Int.n-95 BRA3 4PhBn H Me NO2 1Me-5-Ind C 520 (M⁺ + 1) N-h-62 NA N-h-61 4PhBn H H NO2 1Me-5-Ind C 506 (M⁺ + 1) N-h-63 NB1 Int.n-95 BRA5 4PhBn H Me NO2 5-1HIdz C 507 (M⁺ + 1) N-h-64 NA N-h-63 4PhBn H H NO2 5-1HIdz C 493 (M⁺ + 1) N-h-65 NB1 Int.n-96 BRA1 2CF3Bn H Me NO2 2-Nap C 509 (M⁺ + 1) N-h-66 NA N-h-65 2CF3Bn H H NO2 2-Nap C 495 (M⁺ + 1) N-h-67 NB1 Int.n-96 BRA2 2CF3Bn H Me NO2 5-Ind C 498 (M⁺ + 1) N-h-68 NA N-h-67 2CF3Bn H H NO2 5-Ind C 484 (M⁺ + 1) N-h-69 NB1 Int.n-96 BRA3 2CF3Bn H Me NO2 1Me-5-Ind C 512 (M⁺ + 1) N-h-70 NA N-h-69 2CF3Bn H H NO2 1Me-5-Ind C 498 (M⁺ + 1) N-h-71 NB1 Int.n-96 BRA5 2CF3Bn H Me NO2 5-1HIdz C 499 (M⁺ + 1) N-h-72 NA N-h-71 2CF3Bn H H NO2 5-1HIdz C 485 (M⁺ + 1) N-h-73 NB1 Int.n-97 BRA2 2-TF H Me NO2 5-Ind C 436 (M⁺ + 1) N-h-74 NA N-h-73 2-TF H H NO2 5-Ind C 422 (M⁺ + 1) N-h-75 NB1 Int.n-97 BRA3 2-TF H Me NO2 1Me-5-Ind C 450 (M⁺ + 1) N-h-76 NA N-h-75 2-TF H H NO2 1Me-5-Ind C 436 (M⁺ + 1) N-h-77 NB1 Int.n-97 BRA6 2-TF H Me NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-78 NA N-h-77 2-TF H H NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-h-79 NB1 Int.n-98 BRA2 3-TF H Me NO2 5-Ind C 436 (M⁺ + 1) N-h-80 NA N-h-79 3-TF H H NO2 5-Ind C 422 (M⁺ + 1) N-h-81 NB1 Int.n-98 BRA3 3-TF H Me NO2 1Me-5-Ind C 450 (M⁺ + 1) N-h-82 NA N-h-81 3-TF H H NO2 1Me-5-Ind C 436 (M⁺ + 1) N-h-83 NB1 Int.n-98 BRA5 3-TF H Me NO2 5-1HIdz C 437 (M⁺ + 1) N-h-84 NA N-h-83 3-TF H H NO2 5-1HIdz C 423 (M⁺ + 1) N-h-85 NB1 Int.n-98 BRA5 3-TF H Me NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-86 NA N-h-85 3-TF H H NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-h-87 NB1 Int.n-99 BRA1 2-FR H Me NO2 2-Nap C 459 (M⁺ + 1) N-h-88 NA N-h-87 2-FR H H NO2 2-Nap C 445 (M⁺ + 1) N-h-89 NB1 Int.n-99 BRA2 2-FR H Me NO2 5-Ind C 420 (M⁺ + 1) N-h-90 NA N-h-89 2-FR H H NO2 5-Ind C 406 (M⁺ + 1) N-h-91 NB1 Int.n-99 BRA6 2-FR H Me NO2 1Me-5-1HIdz C 434 (M⁺ + 1) N-h-92 NA N-h-91 2-FR H H NO2 1Me-5-1HIdz C 420 (M⁺ + 1) N-h-93 NB1 Int.n-100 BRA1 Bn Me Me NO2 2-Nap C 455 (M⁺ + 1) N-h-94 NA N-h-93 Bn Me H NO2 2-Nap C 427 (M⁺ + 1) N-h-95 NB1 Int.n-100 BRA2 Bn Me Me NO2 5-Ind C 430 (M⁺ + 1) N-h-96 NA N-h-95 Bn Me H NO2 5-Ind C 416 (M⁺ + 1) N-h-97 NB1 Int.n-100 BRA3 Bn Me Me NO2 1Me-5-Ind C 444 (M⁺ + 1) N-h-98 NA N-h-97 Bn Me H NO2 1Me-5-Ind C 430 (M⁺ + 1) N-h-99 NB1 Int.n-100 BRA5 Bn Me Me NO2 5-1HIdz C 431 (M⁺ + 1) N-h-100 NA N-h-99 Bn Me H NO2 5-1HIdz C 417 (M⁺ + 1) N-h-101 NB1 Int.n-100 BRA5 Bn Me Me NO2 1Me-5-1HIdz C 445 (M⁺ + 1) N-h-102 NA N-h-101 Bn Me H NO2 1Me-5-1HIdz C 431 (M⁺ + 1) N-h-103 NB1 Int.n-100 BRA10 Bn Me Me NO2 3-Qu C 442 (M⁺ + 1) N-h-104 NA N-h-103 Bn Me H NO2 3-Qu C 428 (M⁺ + 1) N-h-105 NB1 Int.n-100 BRA11 Bn Me Me NO2 6-Qu C 442 (M⁺ + 1) N-h-106 NA N-h-105 Bn Me H NO2 6-Qu C 428 (M⁺ + 1) N-h-107 NB1 Int.n-100 BRA12 Bn Me Me NO2 6-IQ C 442 (M⁺ + 1) N-h-108 NA N-h-107 Bn Me H NO2 6-IQ C 428 (M⁺ + 1) N-h-109 NB1 Int.n-101 BRA1 4FBn Me Me NO2 2-Nap C 459 (M⁺ + 1) N-h-110 NA N-h-109 4FBn Me H NO2 2-Nap C 445 (M⁺ + 1) N-h-111 NB1 Int.n-101 BRA2 4FBn Me Me NO2 5-Ind C 448 (M⁺ + 1) N-h-112 NA N-h-111 4FBn Me H NO2 5-Ind C 434 (M⁺ + 1) N-h-113 NB1 Int.n-101 BRA3 4FBn Me Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-114 NA N-h-113 4FBn Me H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-115 NB1 Int.n-101 BRA5 4FBn Me Me NO2 5-1HIdz C 449 (M⁺ + 1) N-h-116 NA N-h-115 4FBn Me H NO2 5-1HIdz C 435 (M⁺ + 1) N-h-117 NB1 Int.n-101 BRA6 4FBn Me Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-118 NA N-h-117 4FBn Me H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-119 NB1 Int.n-102 BRA1 2FBn Me Me NO2 2-Nap C 448 (M⁺ + 1) N-h-120 NA N-h-119 2FBn Me H NO2 2-Nap C 434 (M⁺ + 1) N-h-121 NB1 Int.n-102 BRA3 2FBn Me Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-122 NA N-h-121 2FBn Me H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-123 NB1 Int.n-102 BRA5 2FBn Me Me NO2 5-1HIdz C 449 (M⁺ + 1) N-h-124 NA N-h-123 2FBn Me H NO2 5-1HIdz C 435 (M⁺ + 1) N-h-125 NB1 Int.n-102 BRA5 2FBn Me Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-126 NA N-h-125 2FBn Me H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-127 NB1 Int.n-103 BRA1 3FBn Me Me NO2 2-Nap C 448 (M⁺ + 1) N-h-128 NA N-h-127 3FBn Me H NO2 2-Nap C 434 (M⁺ + 1) N-h-129 NB1 Int.n-103 BRA3 3FBn Me Me NO2 1Me-5-Ind C 462 (M⁺ + 1) N-h-130 NA N-h-129 3FBn Me H NO2 1Me-5-Ind C 448 (M⁺ + 1) N-h-131 NB1 Int.n-103 BRA5 3FBn Me Me NO2 5-1HIdz C 449 (M⁺ + 1) N-h-132 NA N-h-131 3FBn Me H NO2 5-1HIdz C 435 (M⁺ + 1) N-h-133 NB1 Int.n-103 BRA5 3FBn Me Me NO2 1Me-5-1HIdz C 463 (M⁺ + 1) N-h-134 NA N-h-133 3FBn Me H NO2 1Me-5-1HIdz C 449 (M⁺ + 1) N-h-135 NB1 Int.n-104 BRA1 2,3DFBn Me Me NO2 2-Nap C 477 (M⁺ + 1) N-h-136 NA N-h-135 2,3DFBn Me H NO2 2-Nap C 463 (M⁺ + 1) N-h-137 NB1 Int.n-104 BRA3 2,3DFBn Me Me NO2 1Me-5-Ind C 480 (M⁺ + 1) N-h-138 NA N-h-137 2,3DFBn Me H NO2 1Me-5-Ind C 466 (M⁺ + 1) N-h-139 NB1 Int.n-104 BRA5 2,3DFBn Me Me NO2 5-1HIdz C 481 (M⁺ + 1) N-h-140 NA N-h-139 2,3DFBn Me H NO2 5-1HIdz C 467 (M⁺ + 1) N-h-141 NB1 Int.n-104 BRA6 2,3DFBn Me Me NO2 1Me-5-1HIdz C 495 (M⁺ + 1) N-h-142 NA N-h-141 2,3DFBn Me H NO2 1Me-5-1HIdz C 481 (M⁺ + 1) N-h-143 NB1 Int.n-105 BRA1 3,4DFBn Me Me NO2 2-Nap C 480 (M⁺ + 1) N-h-144 NA N-h-143 3,4DFBn Me H NO2 2-Nap C 466 (M⁺ + 1) N-h-145 NB1 Int.n-105 BRA3 3,4DFBn Me Me NO2 1Me-5-Ind C 494 (M⁺ + 1) N-h-146 NA N-h-145 3,4DFBn Me H NO2 1Me-5-Ind C 480 (M⁺ + 1) N-h-147 NB1 Int.n-105 BRA5 3,4DFBn Me Me NO2 1Me-5-1HIdz C 495 (M⁺ + 1) N-h-148 NA N-h-147 3,4DFBn Me H NO2 1Me-5-1HIdz C 481 (M⁺ + 1) N-h-149 NB1 Int.n-106 BRA1 4PhBn Me Me NO2 2-Nap C 531 (M⁺ + 1) N-h-150 NA N-h-149 4PhBn Me H NO2 2-Nap C 517 (M⁺ + 1) N-h-151 NB1 Int.n-106 BRA2 4PhBn Me Me NO2 5-Ind C 520 (M⁺ + 1) N-h-152 NA N-h-151 4PhBn Me H NO2 5-Ind C 506 (M⁺ + 1) N-h-153 NB1 Int.n-106 BRA3 4PhBn Me Me NO2 1Me-5-Ind C 534 (M⁺ + 1) N-h-154 NA N-h-153 4PhBn Me H NO2 1Me-5-Ind C 520 (M⁺ + 1) N-h-155 NB1 Int.n-105 BRA5 4PhBn Me Me NO2 1Me-5-1HIdz C 521 (M⁺ + 1) N-h-156 NA N-h-155 4PhBn Me H NO2 1Me-5-1HIdz C 507 (M⁺ + 1) N-h-157 NB1 Int.n-107 BRA1 2CF3Bn Me Me NO2 2-Nap C 523 (M⁺ + 1) N-h-158 NA N-h-157 2CF3Bn Me H NO2 2-Nap C 509 (M⁺ + 1) N-h-159 NB1 Int.n-107 BRA2 2CF3Bn Me Me NO2 5-Ind C 512 (M⁺ + 1) N-h-160 NA N-h-159 2CF3Bn Me H NO2 5-Ind C 498 (M⁺ + 1) N-h-161 NB1 Int.n-107 BRA3 2CF3Bn Me Me NO2 1Me-5-Ind C 526 (M⁺ + 1) N-h-162 NA N-h-161 2CF3Bn Me H NO2 1Me-5-Ind C 512 (M⁺ + 1) N-h-163 NB1 Int.n-107 BRA5 2CF3Bn Me Me NO2 5-1HIdz C 513 (M⁺ + 1) N-h-164 NA N-h-163 2CF3Bn Me H NO2 5-1HIdz C 499 (M⁺ + 1) N-h-165 NB1 Int.n-108 BRA1 2-TF Me Me NO2 2-Nap C 450 (M⁺ + 1) N-h-166 NA N-h-155 2-TF Me H NO2 2-Nap C 436 (M⁺ + 1) N-h-167 NB1 Int.n-108 BRA3 2-TF Me Me NO2 1Me-5-Ind C 464 (M⁺ + 1) N-h-168 NA N-h-167 2-TF Me H NO2 1Me-5-Ind C 450 (M⁺ + 1) N-h-169 NB1 Int.n-108 BRA6 2-TF Me Me NO2 1Me-5-1HIdz C 465 (M⁺ + 1) N-h-170 NA N-h-169 2-TF Me H NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-171 NB1 Int.n-109 BRA1 3-TF Me Me NO2 2-Nap C 450 (M⁺ + 1) N-h-172 NA N-h-171 3-TF Me H NO2 2-Nap C 436 (M⁺ + 1) N-h-173 NB1 Int.n-109 BRA2 3-TF Me Me NO2 5-Ind C 464 (M⁺ + 1) N-h-174 NA N-h-173 3-TF Me H NO2 5-Ind C 450 (M⁺ + 1) N-h-175 NB1 Int.n-109 BRA3 3-TF Me Me NO2 1Me-5-Ind C 451 (M⁺ + 1) N-h-176 NA N-h-175 3-TF Me H NO2 1Me-5-Ind C 437 (M⁺ + 1) N-h-177 NB1 Int.n-110 BRA6 3-TF Me Me NO2 1Me-5-1HIdz C 465 (M⁺ + 1) N-h-178 NA N-h-177 3-TF Me H NO2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-179 NB1 Int.n-110 BRA1 2-FR Me Me NO2 2-Nap C 473 (M⁺ + 1) N-h-180 NA N-h-179 2-FR Me H NO2 2-Nap C 459 (M⁺ + 1) N-h-181 NB1 Int.n-110 BRA2 2-FR Me Me NO2 5-Ind C 434 (M⁺ + 1) N-h-182 NA N-h-181 2-FR Me H NO2 5-Ind C 420 (M⁺ + 1) N-h-183 NB1 Int.n-109 BRA6 2-FR Me Me NO2 1Me-5-1HIdz C 448 (M⁺ + 1) N-h-184 NA N-h-183 2-FR Me H NO2 1Me-5-1HIdz C 434 (M⁺ + 1) N-h-185 ND1 N-h-1 Bn H Me NH2 2-Nap C 411 (M⁺ + 1) N-h-186 NA N-h-185 Bn H H NH2 2-Nap C 397 (M⁺ + 1) N-h-187 ND1 N-h-3 Bn H Me NH2 5-Ind C 400 (M⁺ + 1) N-h-188 NA N-h-187 Bn H H NH2 5-Ind C 386 (M⁺ + 1) N-h-189 ND1 N-h-5 Bn H Me NH2 1Me-5-Ind C 414 (M⁺ + 1) N-h-190 NA N-h-189 Bn H H NH2 1Me-5-Ind C 400 (M⁺ + 1) N-h-191 ND1 N-h-1 Bn H Me NH2 5-1HIdz C 401 (M⁺ + 1) N-h-192 NA N-h-191 Bn H H NH2 5-1HIdz C 387 (M⁺ + 1) N-h-193 ND1 N-h-9 Bn H Me NH2 1Me-5-1HIdz C 415 (M⁺ + 1) N-h-194 NA N-h-193 Bn H H NH2 1Me-5-1HIdz C 401 (M⁺ + 1) N-h-195 ND1 N-h-11 Bn H Me NH2 3-Qu C 412 (M⁺ + 1) N-h-196 NA N-h-195 Bn H H NH2 3-Qu C 398 (M⁺ + 1) N-h-197 ND1 N-h-13 Bn H Me NH2 6-Qu C 412 (M⁺ + 1) N-h-198 NA N-h-197 Bn H H NH2 6-Qu C 398 (M⁺ + 1) N-h-199 ND1 N-h-17 4FBn H Me NH2 2-Nap C 429 (M⁺ + 1) N-h-200 NA N-h-199 4FBn H H NH2 2-Nap C 415 (M⁺ + 1) N-h-201 ND1 N-h-19 4FBn H Me NH2 5-Ind C 418 (M⁺ + 1) N-h-202 NA N-h-201 4FBn H H NH2 5-Ind C 404 (M⁺ + 1) N-h-203 ND1 N-h-21 4FBn H Me NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-204 NA N-h-203 4FBn H H NH2 1Me-5-Ind C 418 (M⁺ + 1) N-h-205 ND1 N-h-23 4FBn H Me NH2 5-1HIdz C 419 (M⁺ + 1) N-h-206 NA N-h-205 4FBn H H NH2 5-1HIdz C 405 (M⁺ + 1) N-h-207 ND1 N-h-25 4FBn H Me NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-208 NA N-h-207 4FBn H H NH2 1Me-5-1HIdz C 419 (M⁺ + 1) N-h-209 ND1 N-h-27 2FBn H Me NH2 5-Ind C 418 (M⁺ + 1) N-h-210 NA N-h-209 2FBn H H NH2 5-Ind C 404 (M⁺ + 1) N-h-211 ND1 N-h-29 2FBn H Me NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-212 NA N-h-211 2FBn H H NH2 1Me-5-Ind C 418 (M⁺ + 1) N-h-213 ND1 N-h-31 2FBn H Me NH2 5-1HIdz C 419 (M⁺ + 1) N-h-214 NA N-h-213 2FBn H H NH2 5-1HIdz C 405 (M⁺ + 1) N-h-215 ND1 N-h-33 2FBn H Me NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-216 NA N-h-215 2FBn H H NH2 1Me-5-1HIdz C 419 (M⁺ + 1) N-h-217 ND1 N-h-35 3FBn H Me NH2 5-Ind C 418 (M⁺ + 1) N-h-218 NA N-h-217 3FBn H H NH2 5-Ind C 404 (M⁺ + 1) N-h-219 ND1 N-h-37 3FBn H Me NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-220 NA N-h-219 3FBn H H NH2 1Me-5-Ind C 418 (M⁺ + 1) N-h-221 ND1 N-h-39 3FBn H Me NH2 5-1HIdz C 419 (M⁺ + 1) N-h-222 NA N-h-221 3FBn H H NH2 5-1HIdz C 405 (M⁺ + 1) N-h-223 ND1 N-h-41 3FBn H Me NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-224 NA N-h-223 3FBn H H NH2 1Me-5-1HIdz C 419 (M⁺ + 1) N-h-225 ND1 N-h-43 2,3DFBn H Me NH2 2-Nap C 447 (M⁺ + 1) N-h-226 NA N-h-225 2,3DFBn H H NH2 2-Nap C 433 (M⁺ + 1) N-h-227 ND1 N-h-45 2,3DFBn H Me NH2 1Me-5-Ind C 450 (M⁺ + 1) N-h-228 NA N-h-227 2,3DFBn H H NH2 1Me-5-Ind C 436 (M⁺ + 1) N-h-229 ND1 N-h-47 2,3DFBn H Me NH2 5-1HIdz C 437 (M⁺ + 1) N-h-230 NA N-h-229 2,3DFBn H H NH2 5-1HIdz C 423 (M⁺ + 1) N-h-231 ND1 N-h-49 2,3DFBn H Me NH2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-232 NA N-h-231 2,3DFBn H H NH2 1Me-5-1HIdz C 437 (M⁺ + 1) N-h-233 ND1 N-h-51 3,4DFBn H Me NH2 5-Ind C 436 (M⁺ + 1) N-h-234 NA N-h-233 3,4DFBn H H NH2 5-Ind C 422 (M⁺ + 1) N-h-235 ND1 N-h-53 3,4DFBn H Me NH2 1Me-5-Ind C 450 (M⁺ + 1) N-h-236 NA N-h-235 3,4DFBn H H NH2 1Me-5-Ind C 436 (M⁺ + 1) N-h-237 ND1 N-h-55 3,4DFBn H Me NH2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-238 NA N-h-237 3,4DFBn H H NH2 1Me-5-1HIdz C 437 (M⁺ + 1) N-h-239 ND1 N-h-57 4PhBn H Me NH2 2-Nap C 487 (M⁺ + 1) N-h-240 NA N-h-239 4PhBn H H NH2 2-Nap C 473 (M⁺ + 1) N-h-241 ND1 N-h-59 4PhBn H Me NH2 5-Ind C 476 (M⁺ + 1) N-h-242 NA N-h-241 4PhBn H H NH2 5-Ind C 462 (M⁺ + 1) N-h-243 ND1 N-h-61 4PhBn H Me NH2 1Me-5-Ind C 490 (M⁺ + 1) N-h-244 NA N-h-243 4PhBn H H NH2 1Me-5-Ind C 476 (M⁺ + 1) N-h-245 ND1 N-h-63 4PhBn H Me NH2 5-1HIdz C 477 (M⁺ + 1) N-h-246 NA N-h-245 4PhBn H H NH2 5-1HIdz C 463 (M⁺ + 1) N-h-247 ND1 N-h-65 2CF3Bn H Me NH2 2-Nap C 479 (M⁺ + 1) N-h-248 NA N-h-247 2CF3Bn H H NH2 2-Nap C 465 (M⁺ + 1) N-h-249 ND1 N-h-67 2CF3Bn H Me NH2 5-Ind C 468 (M⁺ + 1) N-h-250 NA N-h-249 2CF3Bn H H NH2 5-Ind C 454 (M⁺ + 1) N-h-251 ND1 N-h-69 2CF3Bn H Me NH2 1Me-5-Ind C 482 (M⁺ + 1) N-h-252 NA N-h-251 2CF3Bn H H NH2 1Me-5-Ind C 468 (M⁺ + 1) N-h-253 ND1 N-h-71 2CF3Bn H Me NH2 5-1HIdz C 469 (M⁺ + 1) N-h-254 NA N-h-253 2CF3Bn H H NH2 5-1HIdz C 455 (M⁺ + 1) N-h-255 ND1 N-h-73 2-TF H Me NH2 5-Ind C 406 (M⁺ + 1) N-h-256 NA N-h-255 2-TF H H NH2 5-Ind C 392 (M⁺ + 1) N-h-257 ND1 N-h-75 2-TF H Me NH2 1Me-5-Ind C 420 (M⁺ + 1) N-h-258 NA N-h-257 2-TF H H NH2 1Me-5-Ind C 406 (M⁺ + 1) N-h-259 ND1 N-h-77 2-TF H Me NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-h-260 NA N-h-259 2-TF H H NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-h-261 ND1 N-h-79 3-TF H Me NH2 5-Ind C 406 (M⁺ + 1) N-h-262 NA N-h-261 3-TF H H NH2 5-Ind C 392 (M⁺ + 1) N-h-263 ND1 N-h-81 3-TF H Me NH2 1Me-5-Ind C 420 (M⁺ + 1) N-h-264 NA N-h-263 3-TF H H NH2 1Me-5-Ind C 406 (M⁺ + 1) N-h-265 ND1 N-h-83 3-TF H Me NH2 5-1HIdz C 407 (M⁺ + 1) N-h-266 NA N-h-265 3-TF H H NH2 5-1HIdz C 393 (M⁺ + 1) N-h-267 ND1 N-h-85 3-TF H Me NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-h-268 NA N-h-267 3-TF H H NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-h-269 ND1 N-h-87 2-FR H Me NH2 2-Nap C 401 (M⁺ + 1) N-h-270 NA N-h-269 2-FR H H NH2 2-Nap C 387 (M⁺ + 1) N-h-271 ND1 N-h-89 2-FR H Me NH2 5-Ind C 390 (M⁺ + 1) N-h-272 NA N-h-271 2-FR H H NH2 5-Ind C 376 (M⁺ + 1) N-h-273 ND1 N-h-91 2-FR H Me NH2 1Me-5-1HIdz C 405 (M⁺ + 1) N-h-274 NA N-h-273 2-FR H H NH2 1Me-5-1HIdz C 391 (M⁺ + 1) N-h-275 ND1 N-h-93 Bn Me Me NH2 2-Nap C 425 (M⁺ + 1) N-h-276 NA N-h-275 Bn Me H NH2 2-Nap C 411 (M⁺ + 1) N-h-277 ND1 N-h-95 Bn Me Me NH2 5-Ind C 414 (M⁺ + 1) N-h-278 NA N-h-277 Bn Me H NH2 5-Ind C 400 (M⁺ + 1) N-h-279 ND1 N-h-97 Bn Me Me NH2 1Me-5-Ind C 428 (M⁺ + 1) N-h-280 NA N-h-279 Bn Me H NH2 1Me-5-Ind C 414 (M⁺ + 1) N-h-281 ND1 N-h-99 Bn Me Me NH2 5-1HIdz C 415 (M⁺ + 1) N-h-282 NA N-h-281 Bn Me H NH2 5-1HIdz C 401 (M⁺ + 1) N-h-283 ND1 N-h-101 Bn Me Me NH2 1Me-5-1HIdz C 429 (M⁺ + 1) N-h-284 NA N-h-283 Bn Me H NH2 1Me-5-1HIdz C 415 (M⁺ + 1) N-h-285 ND1 N-h-103 Bn Me Me NH2 3-Qu C 426 (M⁺ + 1) N-h-286 NA N-h-285 Bn Me H NH2 3-Qu C 412 (M⁺ + 1) N-h-287 ND1 N-h-105 Bn Me Me NH2 6-Qu C 426 (M⁺ + 1) N-h-288 NA N-h-287 Bn Me H NH2 6-Qu C 412 (M⁺ + 1) N-h-289 ND1 N-h-107 Bn Me Me NH2 6-IQ C 426 (M⁺ + 1) N-h-290 NA N-h-289 Bn Me H NH2 6-IQ C 412 (M⁺ + 1) N-h-291 ND1 N-h-109 4FBn Me Me NH2 2-Nap C 443 (M⁺ + 1) N-h-292 NA N-h-291 4FBn Me H NH2 2-Nap C 429 (M⁺ + 1) N-h-293 ND1 N-h-111 4FBn Me Me NH2 5-Ind C 432 (M⁺ + 1) N-h-294 NA N-h-293 4FBn Me H NH2 5-Ind C 418 (M⁺ + 1) N-h-295 ND1 N-h-113 4FBn Me Me NH2 1Me-5-Ind C 446 (M⁺ + 1) N-h-296 NA N-h-295 4FBn Me H NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-297 ND1 N-h-115 4FBn Me Me NH2 5-1HIdz C 433 (M⁺ + 1) N-h-298 NA N-h-297 4FBn Me H NH2 5-1HIdz C 419 (M⁺ + 1) N-h-299 ND1 N-h-117 4FBn Me Me NH2 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-300 NA N-h-299 4FBn Me H NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-301 ND1 N-h-119 2FBn Me Me NH2 2-Nap C 443 (M⁺ + 1) N-h-302 NA N-h-301 2FBn Me H NH2 2-Nap C 429 (M⁺ + 1) N-h-303 ND1 N-h-121 2FBn Me Me NH2 1Me-5-Ind C 446 (M⁺ + 1) N-h-304 NA N-h-303 2FBn Me H NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-305 ND1 N-h-123 2FBn Me Me NH2 5-1HIdz C 433 (M⁺ + 1) N-h-306 NA N-h-305 2FBn Me H NH2 5-1HIdz C 419 (M⁺ + 1) N-h-307 ND1 N-h-125 2FBn Me Me NH2 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-308 NA N-h-307 2FBn Me H NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-309 ND1 N-h-127 3FBn Me Me NH2 2-Nap C 443 (M⁺ + 1) N-h-310 NA N-h-309 3FBn Me H NH2 2-Nap C 429 (M⁺ + 1) N-h-311 ND1 N-h-129 3FBn Me Me NH2 1Me-5-Ind C 446 (M⁺ + 1) N-h-312 NA N-h-311 3FBn Me H NH2 1Me-5-Ind C 432 (M⁺ + 1) N-h-313 ND1 N-h-131 3FBn Me Me NH2 5-1HIdz C 433 (M⁺ + 1) N-h-314 NA N-h-313 3FBn Me H NH2 5-1HIdz C 419 (M⁺ + 1) N-h-315 ND1 N-h-133 3FBn Me Me NH2 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-316 NA N-h-315 3FBn Me H NH2 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-317 ND1 N-h-135 2,3DFBn Me Me NH2 2-Nap C 461 (M⁺ + 1) N-h-318 NA N-h-317 2,3DFBn Me H NH2 2-Nap C 447 (M⁺ + 1) N-h-319 ND1 N-h-137 2,3DFBn Me Me NH2 1Me-5-Ind C 464 (M⁺ + 1) N-h-320 NA N-h-319 2,3DFBn Me H NH2 1Me-5-Ind C 450 (M⁺ + 1) N-h-321 ND1 N-h-139 2,3DFBn Me Me NH2 5-1HIdz C 451 (M⁺ + 1) N-h-322 NA N-h-321 2,3DFBn Me H NH2 5-1HIdz C 437 (M⁺ + 1) N-h-323 ND1 N-h-141 2,3DFBn Me Me NH2 1Me-5-1HIdz C 465 (M⁺ + 1) N-h-324 NA N-h-323 2,3DFBn Me H NH2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-325 ND1 N-h-143 3,4DFBn Me Me NH2 2-Nap C 461 (M⁺ + 1) N-h-326 NA N-h-325 3,4DFBn Me H NH2 2-Nap C 447 (M⁺ + 1) N-h-327 ND1 N-h-145 3,4DFBn Me Me NH2 1Me-5-Ind C 464 (M⁺ + 1) N-h-328 NA N-h-327 3,4DFBn Me H NH2 1Me-5-Ind C 450 (M⁺ + 1) N-h-329 ND1 N-h-147 3,4DFBn Me Me NH2 1Me-5-1HIdz C 465 (M⁺ + 1) N-h-330 NA N-h-329 3,4DFBn Me H NH2 1Me-5-1HIdz C 451 (M⁺ + 1) N-h-331 ND1 N-h-149 4PhBn Me Me NH2 2-Nap C 501 (M⁺ + 1) N-h-332 NA N-h-331 4PhBn Me H NH2 2-Nap C 487 (M⁺ + 1) N-h-333 ND1 N-h-151 4PhBn Me Me NH2 5-Ind C 490 (M⁺ + 1) N-h-334 NA N-h-333 4PhBn Me H NH2 5-Ind C 476 (M⁺ + 1) N-h-335 ND1 N-h-153 4PhBn Me Me NH2 1Me-5-Ind C 504 (M⁺ + 1) N-h-336 NA N-h-335 4PhBn Me H NH2 1Me-5-Ind C 490 (M⁺ + 1) N-h-337 ND1 N-h-155 4PhBn Me Me NH2 1Me-5-1HIdz C 505 (M⁺ + 1) N-h-338 NA N-h-337 4PhBn Me H NH2 1Me-5-1HIdz C 491 (M⁺ + 1) N-h-339 ND1 N-h-157 2CF3Bn Me Me NH2 2-Nap C 493 (M⁺ + 1) N-h-340 NA N-h-339 2CF3Bn Me H NH2 2-Nap C 479 (M⁺ + 1) N-h-341 ND1 N-h-159 2CF3Bn Me Me NH2 5-Ind C 482 (M⁺ + 1) N-h-342 NA N-h-341 2CF3Bn Me H NH2 5-Ind C 468 (M⁺ + 1) N-h-343 ND1 N-h-161 2CF3Bn Me Me NH2 1Me-5-Ind C 496 (M⁺ + 1) N-h-344 NA N-h-343 2CF3Bn Me H NH2 1Me-5-Ind C 482 (M⁺ + 1) N-h-345 ND1 N-h-163 2CF3Bn Me Me NH2 5-1HIdz C 483 (M⁺ + 1) N-h-346 NA N-h-345 2CF3Bn Me H NH2 5-1HIdz C 469 (M⁺ + 1) N-h-347 ND1 N-h-165 2-TF Me Me NH2 2-Nap C 431 (M⁺ + 1) N-h-348 NA N-h-347 2-TF Me H NH2 2-Nap C 417 (M⁺ + 1) N-h-349 ND1 N-h-167 2-TF Me Me NH2 1Me-5-Ind C 434 (M⁺ + 1) N-h-350 NA N-h-349 2-TF Me H NH2 1Me-5-Ind C 420 (M⁺ + 1) N-h-351 ND1 N-h-169 2-TF Me Me NH2 1Me-5-1HIdz C 435 (M⁺ + 1) N-h-352 NA N-h-351 2-TF Me H NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-h-353 ND1 N-h-171 3-TF Me Me NH2 2-Nap C 431 (M⁺ + 1) N-h-354 NA N-h-353 3-TF Me H NH2 2-Nap C 417 (M⁺ + 1) N-h-355 ND1 N-h-173 3-TF Me Me NH2 5-Ind C 420 (M⁺ + 1) N-h-356 NA N-h-355 3-TF Me H NH2 5-Ind C 406 (M⁺ + 1) N-h-357 ND1 N-h-175 3-TF Me Me NH2 1Me-5-Ind C 434 (M⁺ + 1) N-h-358 NA N-h-357 3-TF Me H NH2 1Me-5-Ind C 420 (M⁺ + 1) N-h-359 ND1 N-h-177 3-TF Me Me NH2 1Me-5-1HIdz C 435 (M⁺ + 1) N-h-360 NA N-h-359 3-TF Me H NH2 1Me-5-1HIdz C 421 (M⁺ + 1) N-h-361 ND1 N-h-179 2-FR Me Me NH2 2-Nap C 415 (M⁺ + 1) N-h-362 NA N-h-361 2-FR Me H NH2 2-Nap C 401 (M⁺ + 1) N-h-363 ND1 N-h-181 2-FR Me Me NH2 5-Ind C 404 (M⁺ + 1) N-h-364 NA N-h-363 2-FR Me H NH2 5-Ind C 390 (M⁺ + 1) N-h-365 ND1 N-h-183 2-FR Me Me NH2 1Me-5-1HIdz C 419 (M⁺ + 1) N-h-366 NA N-h-365 2-FR Me H NH2 1Me-5-1HIdz C 405 (M⁺ + 1) N-h-367 NN1 N-h-275 CH₃I Bn Me Me NHMe 2-Nap C 439 (M⁺ + 1) N-h-368 NA N-h-367 Bn Me H NHMe 2-Nap C 425 (M⁺ + 1) N-h-369 NN1 N-h-279 CH₃I Bn Me Me NHMe 1Me-5-Ind C 442 (M⁺ + 1) N-h-370 NA N-h-369 Bn Me H NHMe 1Me-5-Ind C 428 (M⁺ + 1) N-h-371 NN1 N-h-283 CH₃I Bn Me Me NHMe 1Me-5-1HIdz C 443 (M⁺ + 1) N-h-372 NA N-h-371 Bn Me H NHMe 1Me-5-1HIdz C 429 (M⁺ + 1) N-h-373 NN1 N-h-285 CH₃I Bn Me Me NHMe 3-Qu C 440 (M⁺ + 1) N-h-374 NA N-h-373 Bn Me H NHMe 3-Qu C 426 (M⁺ + 1) N-h-375 NN1 N-h-289 CH₃I Bn Me Me NHMe 6-IQ C 440 (M⁺ + 1) N-h-376 NA N-h-375 Bn Me H NHMe 6-IQ C 426 (M⁺ + 1) N-h-377 NN1 N-h-291 CH₃I 4FBn Me Me NHMe 2-Nap C 457 (M⁺ + 1) N-h-378 NA N-h-377 4FBn Me H NHMe 2-Nap C 443 (M⁺ + 1) N-h-379 NN1 N-h-295 CH₃I 4FBn Me Me NHMe 1Me-5-Ind C 460 (M⁺ + 1) N-h-380 NA N-h-379 4FBn Me H NHMe 1Me-5-Ind C 446 (M⁺ + 1) N-h-381 NN1 N-h-299 CH₃I 4FBn Me Me NHMe 1Me-5-1HIdz C 461 (M⁺ + 1) N-h-382 NA N-h-381 4FBn Me H NHMe 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-383 NN1 N-h-301 CH₃I 2FBn Me Me NHMe 2-Nap C 457 (M⁺ + 1) N-h-384 NA N-h-383 2FBn Me H NHMe 2-Nap C 443 (M⁺ + 1) N-h-385 NN1 N-h-303 CH₃I 2FBn Me Me NHMe 1Me-5-Ind C 460 (M⁺ + 1) N-h-386 NA N-h-385 2FBn Me H NHMe 1Me-5-Ind C 446 (M⁺ + 1) N-h-387 NN1 N-h-307 CH₃I 2FBn Me Me NHMe 1Me-5-1HIdz C 461 (M⁺ + 1) N-h-388 NA N-h-387 2FBn Me H NHMe 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-389 NN1 N-h-309 CH₃I 3FBn Me Me NHMe 2-Nap C 457 (M⁺ + 1) N-h-390 NA N-h-389 3FBn Me H NHMe 2-Nap C 443 (M⁺ + 1) N-h-391 NN1 N-h-311 CH₃I 3FBn Me Me NHMe 1Me-5-Ind C 460 (M⁺ + 1) N-h-392 NA N-h-391 3FBn Me H NHMe 1Me-5-Ind C 446 (M⁺ + 1) N-h-393 NN1 N-h-317 CH₃I 2,3DFBn Me Me NHMe 2-Nap C 475 (M⁺ + 1) N-h-394 NA N-h-393 2,3DFBn Me H NHMe 2-Nap C 461 (M⁺ + 1) N-h-395 NN1 N-h-323 CH₃I 2,3DFBn Me Me NHMe 1Me-5-1HIdz C 479 (M⁺ + 1) N-h-396 NA N-h-395 2,3DFBn Me H NHMe 1Me-5-1HIdz C 465 (M⁺ + 1) N-h-397 NN1 N-h-327 CH₃I 3,4DFBn Me Me NHMe 1Me-5-Ind C 478 (M⁺ + 1) N-h-398 NA N-h-397 3,4DFBn Me H NHMe 1Me-5-Ind C 464 (M⁺ + 1) N-h-399 NN1 N-h-331 CH₃I 4PhBn Me Me NHMe 2-Nap C 515 (M⁺ + 1) N-h-400 NA N-h-399 4PhBn Me H NHMe 2-Nap C 501 (M⁺ + 1) N-h-401 NN1 N-h-337 CH₃I 4PhBn Me Me NHMe 1Me-5-1HIdz C 519 (M⁺ + 1) N-h-402 NA N-h-401 4PhBn Me H NHMe 1Me-5-1HIdz C 505 (M⁺ + 1) N-h-403 NN1 N-h-339 CH₃I 2CF3Bn Me Me NHMe 2-Nap C 507 (M⁺ + 1) N-h-404 NA N-h-403 2CF3Bn Me H NHMe 2-Nap C 493 (M⁺ + 1) N-h-405 NN1 N-h-343 CH₃I 2CF3Bn Me Me NHMe 1Me-5-Ind C 510 (M⁺ + 1) N-h-406 NA N-h-405 2CF3Bn Me H NHMe 1Me-5-Ind C 496 (M⁺ + 1) N-h-407 NN1 N-h-347 CH₃I 2-TF Me Me NHMe 2-Nap C 445 (M⁺ + 1) N-h-408 NA N-h-407 2-TF Me H NHMe 2-Nap C 431 (M⁺ + 1) N-h-409 NN1 N-h-357 CH₃I 3-TF Me Me NHMe 1Me-5-Ind C 448 (M⁺ + 1) N-h-410 NA N-h-409 3-TF Me H NHMe 1Me-5-Ind C 434 (M⁺ + 1) N-4-411 NN1 N-h-365 CH₃I 2-FR Me Me NHMe 1Me-5-1HIdz C 433 (M⁺ + 1) N-h-412 NA N-h-411 2-FR Me H NHMe 1Me-5-1HIdz C 419 (M⁺ + 1) N-h-413 NN2 N-h-275 CH₃I Bn Me Me NMe2 2-Nap C 453 (M⁺ + 1) N-h-414 NA N-h-413 Bn Me H NMe2 2-Nap C 439 (M⁺ + 1) N-h-415 NN2 N-h-279 CH₃I Bn Me Me NMe2 1Me-5-Ind C 456 (M⁺ + 1) N-h-416 NA N-h-415 Bn Me H NMe2 1Me-5-Ind C 442 (M⁺ + 1) N-h-417 NN2 N-h-283 CH₃I Bn Me Me NMe2 1Me-5-1HIdz C 457 (M⁺ + 1) N-h-418 NA N-h-417 Bn Me H NMe2 1Me-5-1HIdz C 443 (M⁺ + 1) N-h-419 NN2 N-h-285 CH₃I Bn Me Me NMe2 3-Qu C 454 (M⁺ + 1) N-h-420 NA N-h-419 Bn Me H NMe2 3-Qu C 440 (M⁺ + 1) N-h-421 NN2 N-h-289 CH₃I Bn Me Me NMe2 6-IQ C 454 (M⁺ + 1) N-h-422 NA N-h-421 Bn Me H NMe2 6-IQ C 440 (M⁺ + 1) N-h-423 NN2 N-h-291 CH₃I 4FBn Me Me NMe2 2-Nap C 471 (M⁺ + 1) N-h-424 NA N-h-423 4FBn Me H NMe2 2-Nap C 457 (M⁺ + 1) N-h-425 NN2 N-h-295 CH₃I 4FBn Me Me NMe2 1Me-5-Ind C 474 (M⁺ + 1) N-h-426 NA N-h-425 4FBn Me H NMe2 1Me-5-Ind C 460 (M⁺ + 1) N-h-427 NN2 N-h-299 CH₃I 4FBn Me Me NMe2 1Me-5-1HIdz C 475 (M⁺ + 1) N-h-428 NA N-h-427 4FBn Me H NMe2 1Me-5-1HIdz C 461 (M⁺ + 1) N-h-429 NN2 N-h-301 CH₃I 2FBn Me Me NMe2 2-Nap C 471 (M⁺ + 1) N-h-430 NA N-h-429 2FBn Me H NMe2 2-Nap C 457 (M⁺ + 1) N-h-431 NN2 N-h-303 CH₃I 2FBn Me Me NMe2 1Me-5-Ind C 474 (M⁺ + 1) N-h-432 NA N-h-431 2FBn Me H NMe2 1Me-5-Ind C 460 (M⁺ + 1) N-h-433 NN2 N-h-307 CH₃I 2FBn Me Me NMe2 1Me-5-1HIdz C 475 (M⁺ + 1) N-h-434 NA N-h-433 2FBn Me H NMe2 1Me-5-1HIdz C 461 (M⁺ + 1) N-h-435 NN2 N-h-309 CH₃I 3FBn Me Me NMe2 2-Nap C 471 (M⁺ + 1) N-h-436 NA N-h-435 3FBn Me H NMe2 2-Nap C 457 (M⁺ + 1) N-h-437 NN2 N-h-311 CH₃I 3FBn Me Me NMe2 1Me-5-Ind C 474 (M⁺ + 1) N-h-438 NA N-h-437 3FBn Me H NMe2 1Me-5-Ind C 460 (M⁺ + 1) N-h-439 NN2 N-h-317 CH₃I 2,3DFBn Me Me NMe2 2-Nap C 489 (M⁺ + 1) N-h-440 NA N-h-439 2,3DFBn Me H NMe2 2-Nap C 475 (M⁺ + 1) N-h-441 NN2 N-h-323 CH₃I 2,3DFBn Me Me NMe2 1Me-5-1HIdz C 493 (M⁺ + 1) N-h-442 NA N-h-441 2,3DFBn Me H NMe2 1Me-5-1HIdz C 479 (M⁺ + 1) N-h-443 NN2 N-h-327 CH₃I 3,4DFBn Me Me NMe2 1Me-5-Ind C 492 (M⁺ + 1) N-h-444 NA N-h-443 3,4DFBn Me H NMe2 1Me-5-Ind C 478 (M⁺ + 1) N-h-445 NN2 N-h-331 CH₃I 4PhBn Me Me NMe2 2-Nap C 529 (M⁺ + 1) N-h-446 NA N-h-445 4PhBn Me H NMe2 2-Nap C 515 (M⁺ + 1) N-h-447 NN2 N-h-337 CH₃I 4PhBn Me Me NMe2 1Me-5-1HIdz C 533 (M⁺ + 1) N-h-448 NA N-h-447 4PhBn Me H NMe2 1Me-5-1HIdz C 519 (M⁺ + 1) N-h-449 NN2 N-h-339 CH₃I 2CF3Bn Me Me NMe2 2-Nap C 521 (M⁺ + 1) N-h-450 NA N-h-449 2CF3Bn Me H NMe2 2-Nap C 507 (M⁺ + 1) N-h-451 NN2 N-h-343 CH₃I 2CF3Bn Me Me NMe2 1Me-5-Ind C 524 (M⁺ + 1) N-h-452 NA N-h-451 2CF3Bn Me H NMe2 1Me-5-Ind C 510 (M⁺ + 1) N-h-453 NN2 N-h-347 CH₃I 2-TF Me Me NMe2 2-Nap C 459 (M⁺ + 1) N-h-454 NA N-h-453 2-TF Me H NMe2 2-Nap C 445 (M⁺ + 1) N-h-455 NN2 N-h-357 CH₃I 3-TF Me Me NMe2 1Me-5-Ind C 462 (M⁺ + 1) N-h-456 NA N-h-455 3-TF Me H NMe2 1Me-5-Ind C 448 (M⁺ + 1) N-h-457 NN2 N-h-365 CH₃I 2-FR Me Me NMe2 1Me-5-1HIdz C 447 (M⁺ + 1) N-h-458 NA N-h-457 2-FR Me H NMe2 1Me-5-1HIdz C 433 (M⁺ + 1)

Examples N-I-1 to N-I-138

Typical examples of the compounds of the present invention that can be obtained by reacting and treating corresponding starting compounds using any of the methods described in the present specification are shown in Table-N-I-1 to Table-N-I-8. In the tables, the compound numbers are mentioned in the columns indicated as “Exp.”. In the tables, used methods among the aforementioned synthesis methods are shown in the columns of “Syn” with symbols, the starting compounds 1 are mentioned in the columns of “SM1”, and the starting compounds 2 are mentioned in the columns of “SM2”.

TABLE N-I-1

LCMS Exp. Syn SM1 SM2 NRzRy Y Zx AR method RTime Mass N-i-1 NB1 Int.n-111 BRA1

Me NO2 2-Nap C 405 (M⁺ + 1) N-i-2 NA N-i-1

H NO2 2-Nap C 391 (M⁺ + 1) N-i-3 NB1 Int.n-111 BRA2

Me NO2 5-1Ind C 394 (M⁺ + 1) N-i-4 NA N-i-3

H NO2 5-1Ind C 380 (M⁺ + 1) N-i-5 NB1 Int.n-111 BRA3

Me NO2 1Me-5-Ind C 408 (M⁺ + 1) N-i-6 NA N-i-5

H NO2 1Me-5-Ind C 394 (M⁺ + 1) N-i-7 NB1 Int.n-111 BRA5

Me NO2 5-1HIdz C 395 (M⁺ + 1) N-i-8 NA N-i-7

H NO2 5-1HIdz C 381 (M⁺ + 1) N-i-9 NB1 Int.n-111 BRA6

Me NO2 1Me-5-1HIdz C 409 (M⁺ + 1) N-i-10 NA N-i-9

H NO2 1Me-5-1HIdz C 395 (M⁺ + 1) N-i-11 NB1 Int.n-111 BRA9

Me NO2 5-Bzt C 412 (M⁺ + 1) N-i-12 NA N-i-11

H NO2 5-Bzt C 398 (M⁺ + 1) N-i-13 NB1 Int.n-111 BRA10

Me NO2 3-Qu C 406 (M⁺ + 1) N-i-14 NA N-i-13

H NO2 3-Qu C 392 (M⁺ + 1) N-i-15 NB1 Int.n-111 BRA11

Me NO2 6-Qu C 406 (M⁺ + 1) N-i-16 NA N-i-15

H NO2 6-Qu C 392 (M⁺ + 1) N-i-17 NB1 Int.n-112 BRA1

Me NO2 2-Nap C 421 (M⁺ + 1) N-i-18 NA N-i-17

H NO2 2-Nap C 407 (M⁺ + 1) N-i-19 NB1 Int.n-112 BRA2

Me NO2 5-1Ind C 410 (M⁺ + 1) N-i-20 NA N-i-19

H NO2 5-1Ind C 396 (M⁺ + 1) N-i-21 NB1 Int.n-112 BRA3

Me NO2 1Me-5-Ind C 424 (M⁺ + 1) N-i-22 NA N-i-21

H NO2 1Me-5-Ind C 410 (M⁺ + 1) N-i-23 NB1 Int.n-112 BRA5

Me NO2 5-1HIdz C 411 (M⁺ + 1) N-i-24 NA N-i-23

H NO2 5-1HIdz C 391 (M⁺ + 1) N-i-25 NB1 Int.n-112 BRA6

Me NO2 1Me-5-1HIdz C 425 (M⁺ + 1) N-i-26 NA N-i-25

H NO2 1Me-5-1HIdz C 411 (M⁺ + 1) N-i-27 NB1 Int.n-113 BRA1

Me NO2 2-Nap C 419 (M⁺ + 1) N-i-28 NA N-i-27

H NO2 2-Nap C 405 (M⁺ + 1) N-i-29 NB1 Int.n-113 BRA2

Me NO2 5-1Ind C 408 (M⁺ + 1) N-i-30 NA N-i-29

H NO2 5-1Ind C 394 (M⁺ + 1) N-i-31 NB1 Int.n-113 BRA3

Me NO2 1Me-5-Ind C 422 (M⁺ + 1) N-i-32 NA N-i-31

H NO2 1Me-5-Ind C 408 (M⁺ + 1) N-i-33 NB1 Int.n-113 BRA5

Me NO2 5-1HIdz C 409 (M⁺ + 1) N-i-34 NA N-i-33

H NO2 5-1HIdz C 395 (M⁺ + 1) N-i-35 NB1 Int.n-113 BRA6

Me NO2 1Me-5-1HIdz C 423 (M⁺ + 1) N-i-36 NA N-i-35

H NO2 1Me-5-1HIdz C 409 (M⁺ + 1) N-i-37 NB1 Int.n-113 BRA11

Me NO2 6-Qu C 420 (M⁺ + 1) N-i-38 NA N-i-37

H NO2 6-Qu C 406 (M⁺ + 1) N-i-39 NB1 Int.n-114 BRA1

Me NO2 2-Nap C 433 (M⁺ + 1) N-i-40 NA N-i-39

H NO2 2-Nap C 419 (M⁺ + 1) N-i-41 NB1 Int.n-114 BRA3

Me NO2 1Me-5-Ind C 437 (M⁺ + 1) N-i-42 NA N-i-41

H NO2 1Me-5-Ind C 423 (M⁺ + 1) N-i-43 NB1 Int.n-114 BRA5

Me NO2 5-1HIdz C 423 (M⁺ + 1) N-i-44 NA N-i-43

H NO2 5-1HIdz C 409 (M⁺ + 1) N-i-45 NB1 Int.n-114 BRA6

Me NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-i-46 NA N-i-45

H NO2 1Me-5-1HIdz C 423 (M⁺ + 1) N-i-47 NB1 Int.n-115 BRA3

Me NO2 1Me-5-Ind C 436 (M⁺ + 1) N-i-48 NA N-i-47

H NO2 1Me-5-Ind C 422 (M⁺ + 1) N-i-49 NB1 Int.n-115 BRA5

Me NO2 5-1HIdz C 423 (M⁺ + 1) N-i-50 NA N-i-49

H NO2 5-1HIdz C 409 (M⁺ + 1) N-i-51 NB1 Int.n-115 BRA6

Me NO2 1Me-5-1HIdz C 437 (M⁺ + 1) N-i-52 NA N-i-51

H NO2 1Me-5-IHIdz C 423 (M⁺ + 1) N-i-53 ND1 N-i-1

Me NH2 2-Nap C 375 (M⁺ + 1) N-i-54 NA N-i-53

H NH2 2-Nap C 361 (M⁺ + 1) N-i-55 ND1 N-i-3

Me NH2 5-1Ind C 364 (M⁺ + 1) N-i-56 NA N-i-55

H NH2 5-1Ind C 350 (M⁺ + 1) N-i-57 ND1 N-i-5

Me NH2 1Me-5-Ind C 378 (M⁺ + 1) N-i-58 NA N-i-57

H NH2 1Me-5-Ind C 364 (M⁺ + 1) N-i-59 ND1 N-i-7

Me NH2 5-1HIdz C 365 (M⁺ + 1) N-i-60 NA N-i-59

H NH2 5-1HIdz C 351 (M⁺ + 1) N-i-61 ND1 N-i-9

Me NH2 1Me-5-1HIdz C 379 (M⁺ + 1) N-i-62 NA N-i-61

H NH2 1Me-5-1HIdz C 365 (M⁺ + 1) N-i-63 ND1 N-i-11

Me NH2 5-Bzt C 382 (M⁺ + 1) N-i-64 NA N-i-63

H NH2 5-Bzt C 368 (M⁺ + 1) N-i-65 ND1 N-i-13

Me NH2 3-Qu C 376 (M⁺ + 1) N-i-66 NA N-i-65

H NH2 3-Qu C 362 (M⁺ + 1) N-i-67 ND1 N-i-15

Me NH2 6-Qu C 376 (M⁺ + 1) N-i-68 NA N-i-67

H NH2 6-Qu C 362 (M⁺ + 1) N-i-69 ND1 N-i-17

Me NH2 2-Nap C 391 (M⁺ + 1) N-i-70 NA N-i-69

H NH2 2-Nap C 377 (M⁺ + 1) N-i-71 ND1 N-i-19

Me NH2 5-1Ind C 380 (M⁺ + 1) N-i-72 NA N-i-71

H NH2 5-1Ind C 366 (M⁺ + 1) N-i-73 ND1 N-i-21

Me NH2 1Me-5-Ind C 394 (M⁺ + 1) N-i-74 NA N-i-73

H NH2 1Me-5-Ind C 380 (M⁺ + 1) N-i-75 ND1 N-i-23

Me NH2 5-1HIdz C 381 (M⁺ + 1) N-i-76 NA N-i-75

H NH2 5-1HIdz C 367 (M⁺ + 1) N-i-77 ND1 N-i-25

Me NH2 1Me-5-1HIdz C 395 (M⁺ + 1) N-i-78 NA N-i-77

H NH2 1Me-5-1HIdz C 381 (M⁺ + 1) N-i-79 ND1 N-i-27

Me NH2 2-Nap C 389 (M⁺ + 1) N-i-80 NA N-i-79

H NH2 2-Nap C 375 (M⁺ + 1) N-i-81 ND1 N-i-29

Me NH2 5-1Ind C 378 (M⁺ + 1) N-i-82 NA N-i-81

H NH2 5-1Ind C 364 (M⁺ + 1) N-i-83 ND1 N-i-31

Me NH2 1Me-5-Ind C 392 (M⁺ + 1) N-i-84 NA N-i-83

H NH2 1Me-5-Ind C 378 (M⁺ + 1) N-i-85 ND1 N-i-33

Me NH2 5-1HIdz C 379 (M⁺ + 1) N-i-86 NA N-i-85

H NH2 5-1HIdz C 365 (M⁺ + 1) N-i-87 ND1 N-i-35

Me NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-88 NA N-i-87

H NH2 1Me-5-1HIdz C 379 (M⁺ + 1) N-i-89 ND1 N-i-37

Me NH2 6-Qu C 390 (M⁺ + 1) N-i-90 NA N-i-89

H NH2 6-Qu C 376 (M⁺ + 1) N-i-91 ND1 N-i-39

Me NH2 2-Nap C 403 (M⁺ + 1) N-i-92 NA N-i-91

H NH2 2-Nap C 389 (M⁺ + 1) N-i-93 ND1 N-i-41

Me NH2 1Me-5-Ind C 406 (M⁺ + 1) N-i-94 NA N-i-93

H NH2 1Me-5-Ind C 392 (M⁺ + 1) N-i-95 ND1 N-i-43

Me NH2 5-1Idz C 393 (M⁺ + 1) N-i-96 NA N-i-95

H NH2 5-1Idz C 379 (M⁺ + 1) N-i-97 ND1 N-i-45

Me NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-98 NA N-i-97

H NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-99 ND1 N-i-47

Me NH2 1Me-5-Ind C 406 (M⁺ + 1) N-i-100 NA N-i-99

H NH2 1Me-5-Ind C 392 (M⁺ + 1) N-i-101 ND1 N-i-49

Me NH2 5-1Idz C 393 (M⁺ + 1) N-i-102 NA N-i-101

H NH2 5-1Idz C 379 (M⁺ + 1) N-i-103 ND1 N-i-51

Me NH2 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-104 NA N-i-103

H NH2 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-105 NN1 N-i-53 CH₃I

Me NHMe 2-Nap C 389 (M⁺ + 1) N-i-106 NA N-i-105

H NHMe 2-Nap C 375 (M⁺ + 1) N-i-107 NN1 N-i-57 CH₃I

Me NHMe 1Me-5-Ind C 392 (M⁺ + 1) N-i-108 NA N-i-107

H NHMe 1Me-5-Ind C 378 (M⁺ + 1) N-i-109 NN1 N-i-61 CH₃I

Me NHMe 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-110 NA N-i-109

H NHMe 1Me-5-1HIdz C 379 (M⁺ + 1) N-i-111 NN1 N-i-63 CH₃I

Me NHMe 5-Bzt C 396 (M⁺ + 1) N-i-112 NA N-i-111

H NHMe 5-Bzt C 382 (M⁺ + 1) N-i-113 NN1 N-i-65 CH₃I

Me NHMe 3-Qu C 390 (M⁺ + 1) N-i-114 NA N-i-113

H NHMe 3-Qu C 376 (M⁺ + 1) N-i-115 NN1 N-i-67 CH₃I

Me NHMe 6-Qu C 390 (M⁺ + 1) N-i-116 NA N-i-115

H NHMe 6-Qu C 376 (M⁺ + 1) N-i-117 NN1 N-i-69 CH₃I

Me NHMe 2-Nap C 405 (M⁺ + 1) N-i-118 NA N-i-117

H NHMe 2-Nap C 391 (M⁺ + 1) N-i-119 NN1 N-i-73 CH₃I

Me NHMe 1Me-5-Ind C 408 (M⁺ + 1) N-i-120 NA N-i-119

H NHMe 1Me-5-Ind C 394 (M⁺ + 1) N-i-121 NN1 N-i-77 CH₃I

Me NHMe 1Me-5-1HIdz C 409 (M⁺ + 1) N-i-122 NA N-i-121

H NHMe 1Me-5-1HIdz C 395 (M⁺ + 1) N-i-123 NN1 N-i-79 CH₃I

Me NHMe 2-Nap C 403 (M⁺ + 1) N-i-124 NA N-i-123

H NHMe 2-Nap C 389 (M⁺ + 1) N-i-125 NN1 N-i-83 CH₃I

Me NHMe 1Me-5-Ind C 406 (M⁺ + 1) N-i-126 NA N-i-125

H NHMe 1Me-5-Ind C 392 (M⁺ + 1) N-i-127 NN1 N-i-87 CH₃I

Me NHMe 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-128 NA N-i-127

H NHMe 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-129 NN1 N-i-91 CH₃I

Me NHMe 2-Nap C 417 (M⁺ + 1) N-i-130 NA N-i-129

H NHMe 2-Nap C 403 (M⁺ + 1) N-i-131 NN1 N-i-93 CH₃I

Me NHMe 1Me-5-Ind C 420 (M⁺ + 1) N-i-132 NA N-i-131

H NHMe 1Me-5-Ind C 406 (M⁺ + 1) N-i-133 NN1 N-i-97 CH₃I

Me NHMe 1Me-5-1HIdz C 421 (M⁺ + 1) N-i-134 NA N-i-133

H NHMe 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-135 NN1 N-199 CH₃I

Me NHMe 1Me-5-Ind C 420 (M⁺ + 1) N-i-136 NA N-i-135

H NHMe 1Me-5-Ind C 406 (M⁺ + 1) N-i-137 NN1 N-i-103 CH₃I

Me NHMe 1Me-5-1HIdz C 421 (M⁺ + 1) N-i-138 NA N-i-137

H NHMe 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-139 NN2 N-i-53 CH₃I

Me NMe2 2-Nap C 403 (M⁺ + 1) N-i-140 NA N-i-139

H NMe2 2-Nap C 389 (M⁺ + 1) N-i-141 NN2 N-i-57 CH₃I

Me NMe2 1Me-5-Ind C 406 (M⁺ + 1) N-i-142 NA N-i-141

H NMe2 1Me-5-Ind C 392 (M⁺ + 1) N-i-143 NN2 N-i-61 CH₃I

Me NMe2 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-144 NA N-i-143

H NMe2 1Me-5-1HIdz C 393 (M⁺ + 1) N-i-145 NN2 N-i-63 CH₃I

Me NMe2 5-Bzt C 410 (M⁺ + 1) N-i-146 NA N-i-145

H NMe2 5-Bzt C 396 (M⁺ + 1) N-i-147 NN2 N-i-65 CH₃I

Me NMe2 3-Qu C 404 (M⁺ + 1) N-i-148 NA N-i-147

H NMe2 3-Qu C 390 (M⁺ + 1) N-i-149 NN2 N-i-67 CH₃I

Me NMe2 6-Qu C 404 (M⁺ + 1) N-i-150 NA N-i-149

H NMe2 6-Qu C 390 (M⁺ + 1) N-i-151 NN2 N-i-69 CH₃I

Me NMe2 2-Nap C 419 (M⁺ + 1) N-i-152 NA N-i-151

H NMe2 2-Nap C 405 (M⁺ + 1) N-i-153 NN2 N-i-73 CH₃I

Me NMe2 1Me-5-Ind C 422 (M⁺ + 1) N-i-154 NA N-i-153

H NMe2 1Me-5-Ind C 408 (M⁺ + 1) N-i-121 NN2 N-i-77 CH₃I

Me NMe2 1Me-5-1HIdz C 423 (M⁺ + 1) N-i-122 NA N-i-121

H NMe2 1Me-5-1HIdz C 409 (M⁺ + 1) N-i-123 NN2 N-i-79 CH₃I

Me NMe2 2-Nap C 417 (M⁺ + 1) N-i-124 NA N-i-123

H NMe2 2-Nap C 403 (M⁺ + 1) N-i-125 NN2 N-i-83 CH₃I

Me NMe2 1Me-5-Ind C 420 (M⁺ + 1) N-i-126 NA N-i-125

H NMe2 1Me-5-Ind C 406 (M⁺ + 1) N-i-127 NN2 N-i-87 CH₃I

Me NMe2 1Me-5-1HIdz C 421 (M⁺ + 1) N-i-128 NA N-i-127

H NMe2 1Me-5-1HIdz C 407 (M⁺ + 1) N-i-129 NN2 N-i-91 CH₃I

Me NMe2 2-Nap C 431 (M⁺ + 1) N-i-130 NA N-i-129

H NMe2 2-Nap C 417 (M⁺ + 1) N-i-131 NN2 N-i-93 CH₃I

Me NMe2 1Me-5-Ind C 434 (M⁺ + 1) N-i-132 NA N-i-131

H NMe2 1Me-5-Ind C 420 (M⁺ + 1) N-i-133 NN2 N-i-97 CH₃I

Me NMe2 1Me-5-1HIdz C 435 (M⁺ + 1) N-i-134 NA N-i-133

H NMe2 1Me-5-1HIdz C 421 (M⁺ + 1) N-i-135 NN2 N-i-99 CH₃I

Me NMe2 2-Nap C 431 (M⁺ + 1) N-i-136 NA N-i-135

H NMe2 2-Nap C 417 (M⁺ + 1) N-i-137 NN2 N-i-103 CH₃I

Me NMe2 1Me-5-1HIdz C 435 (M⁺ + 1) N-i-138 NA N-i-137

H NMe2 1Me-5-1HIdz C 421 (M⁺ + 1)

Test Examples 1. Suppressing Action on PGE₂ Production from IL-1β-stimulated MG-63 Cells (1) Method for Measurement

An action of suppressing PGE₂ production caused by interleukin (IL) 1β as an inflammatory stimulant was studied by the following method. Cells of MG-63, which is a human osteosarcoma cell line (purchased from Dainippon Pharmaceutical), were suspended in EMEM medium (GIBCO) containing 10% fetal bovine serum (BioFluid), and then inoculated to each well of 96-well culture plate at a density of 2×10⁴ cells/well and cultured overnight. The medium was changed to EMEM medium containing 0.5% fetal bovine serum, and then a test compound was added to each well. Human interleukin-1β (ENDOGEN) was further added as an inflammatory stimulant at a final concentration of 1 ng/ml. The cells were further cultured for 18 hours. Then, the culture supernatant was collected, and the PGE₂ concentration in the culture supernatant was measured by using EIA kit (CAYMAN). By using a well which was not added with the stimulant as a negative control and a well which was added only with the stimulant as a positive control, suppression ratio on PGE₂ production was calculated from the produced amount of PGE₂ in the well added with the test compound using the following equation.

PGE ₂ production suppression ratio=[1−(C−B)/(A−B)]×100  [Equation 1]

A: PGE₂ production amount of positive control

B: PGE₂ production amount of negative control

C: PGE₂ production amount in well added with test compound

Further, cytotoxicity of the compounds was studied by using the cells after the collection of the supernatant according to the methylene blue uptake method. Specifically, the cells remained after the collection of the supernatant were fixed with glutaraldehyde and stained with a 0.05% methylene blue solution, then methylene blue taken up by the cells was extracted with 0.3 N hydrochloric acid, and absorbance of the extract was measured at 670 nm. The absorbance of the well of the aforementioned positive control was taken as 100%, and a test compound that gave absorbance in well of less than 80% was judged to be positive in cytotoxicity.

(2) Measurement Results

The test compounds (Compound Nos. G-1 to G-121, H-1 to H-32, J-1 to J-92, K-1 to K-40, L-1 to L-95, M-1 to M-32, N-1 to N-74, P-1 to P-50, Q-1 to Q-52, S-1 to S-73, T-1 to T-61, U-1 to U-18, V-1 to V-109, and W-1 to W-13) suppressed the PGE₂ production caused by IL-1β by 50% or more at 1.0 μM. Moreover, all the test compounds did not exhibit cytotoxicity at that concentration.

The test compounds (Compound Nos. Ca-1 to Ca-203) suppressed the PGE₂ production caused by IL-1β by 50% or more at 1.0 μM. None of the test compounds exhibited cytotoxicity at that concentration.

The test compounds (Compound Nos. S-a-1 to S-a-24, S-b-1 to S-b-138, and S-c-1 to S-c-138) suppressed the PGE₂ production caused by IL-1 by 50% or more at 1.0 μM. None of the test compounds exhibited cytotoxicity at that concentration.

Further, the test compounds (Compound Nos. N-a-1 to N-a-142, N-b-1 to N-b-182, N-c-1 to N-c-64, N-d-1 to N-d-74, N-e-1 to N-e-186 and N-g-1 to N-g-44) suppressed the PGE₂ production caused by IL-1β by 50% or more at 1.0 μM. None of the test compounds exhibited cytotoxicity at that concentration.

Therefore, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention are useful as agents for suppressing inflammatory prostaglandin production.

2. Suppressing Action on PGD₂ and LTB₄ Production from IgE-Stimulated RBL-2H3 Cells (1) Method for Measurement

Suppressing action on PGD₂ and LTB₄ production caused by IgE as an allergic stimulant was investigated by the following method. Cells of RBL-2H3, which is a rat mastocytoma cell line (purchased from ATCC), were suspended in DEMEM medium (GIBCO) containing 10% fetal bovine serum (BioFluid), inoculated to each well of 48-well culture plate at a density of 2×10⁴ cells/well and cultured overnight. Then, IgE antiserum directed to dinitrophenylated BSA (hereinafter abbreviated as “DNP-BSA”) was further added to each well, and the cells were cultured for 30 minutes. Then, the medium was changed to DEMEM medium containing 0.5% fetal bovine serum, a test compound was added to each well, and DNP-BSA was further added at a final concentration of 100 ng/ml as a stimulant. Ten minutes after the stimulant was added, the culture supernatant was collected, and the PGD₂ concentration and LTB₄ concentration in the culture supernatant were measured by using EIA kit (CAYMAN). By using a well which was not added with the stimulant as a negative control and a well which was added only with the stimulant as a positive control, suppressing ratios on mediator production were calculated from the production amounts of the mediators in the well added with the test compound using the following equation 2.

PGD ₂ or LTB ₄ production suppression ratio=[1−(C−B)/(A−B)]×100  [Equation 2]

A: PGD₂ or LTB₄ production amount of positive control

B: PGD₂ or LTB₄ production amount of negative control

C: PGD₂ or LTB₄ production amount in well added with test compound

Cytotoxicity of the compounds was studied in the same manner as those described above, by using the cells after the collection of the supernatant according to the methylene blue uptake method.

(2) Measurement Results

Representative compounds of the objective Compounds (I) described in the specification suppressed the PGD₂ and LTB₄ production caused by IgE stimulation by 50% or more at 1.0 μM. Moreover, all the test compounds did not exhibit cytotoxicity at that concentration. Thus, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention exhibit suppressing action on the allergic prostaglandin and leukotriene production, and are useful as suppressing agents for the production thereof.

3. Suppressing Effect on Mouse Zymosan-Stimulated Footpad Edema Reaction (1) Method for Measurement

A suppressing effect on footpad edema caused by zymosan as an inflammatory stimulant was studied by the following method. Groups of ICR female mice (6- to 7-week old) each consisting of eight mice were used for the test. A test compound was suspended or dissolved in purified water containing 0.5% methylcellulose and orally administered to the test animals at 0.1 to 500 mg/10 ml/kg. To the control group, purified water containing 0.5% methylcellulose was administered in a similar manner, which was not added with a test compound. One hour after the administration of the test compound, 0.02 ml of a suspension of zymosan suspended in physiological saline (Otsuka Pharmaceutical) at 1 mg/ml was subcutaneously administered to right hind leg footpad of each mouse. One and two hours after the administration of the zymosan suspension, volume of the right hind leg footpad was measured by using an apparatus for measuring a volume of mouse hind leg footpad edema (Unicom). A difference of the volume of footpad measured above and the footpad volume before the administration of the test compound measured beforehand was regarded as a volume of the edema.

For the volume of the edema at 1 hour or 2 hours after the zymosan administration, a graph was prepared by indicating time in abscissa and the edema volume in ordinate, and an edema volume AUC (area under the curve) was obtained up to 2 hours by calculation using the following equation.

Edema volume AUC(μl·hour)=½×1×A+1×(A+B)/2  [Equation 3]

A: Edema volume 1 hour after zymosan administration

B: Edema volume 2 hour after zymosan administration

A suppression ratio on edema of test compound was obtained by calculation using the following equation.

Edema suppression ratio(%)=[1−B/A]×100  [Equation 4]

A: Edema volume AUC of positive control

B: Edema volume AUC of test compound administered group

(2) Measurement Results

Representative compounds of the objective Compounds (I) described in the specification more effectively suppressed footpad edema caused by subcutaneous administration of zymosan compared with the positive control group by oral administration at 0.1 to 500 mg/kg.

Therefore, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention exhibit a suppressing action on footpad edema caused by zymosan as an inflammatory stimulant, and thus they are useful as agents for prophylactic and/or therapeutic drugs for inflammatory diseases.

4. Suppressing Effect on Mouse IgE-Stimulated Footpad Edema Reaction (1) Method for Measurement

Suppression on footpad edema caused by IgE antibody as an allergic stimulant was studied by the following method. Groups of C⁵⁷BL/6 male mice (9- to 11-week old) each consisting of five mice were used for the test. Anti-DNP-BSA IgE serum was subcutaneously administered in a volume of 20 μl to right hind leg footpad of each mouse one day before the test. A test compound was suspended or dissolved in purified water containing 0.5% methylcellulose and orally administered to the test animals at 0.1 to 500 mg/10 ml/kg. To the control group, purified water containing 0.5% methylcellulose was administered in a similar manner, which was not added with any test compound. Two hours after the administration of the test compound, 0.2 ml of a solution of DNP-BSA dissolved in physiological saline (Otsuka Pharmaceutical) at 2.5 μg/ml was intravenously administered. The thickness of right hind leg footpad was measured by using a digital thickness gauge (MITSUTOYO) 10, 15, 20, and 30 minutes after the administration of DNP-BSA. A difference of the thickness of footpad measured above and the thickness before the administration of the test compound measured beforehand was regarded as a thickness of edema.

For the thickness of the edema at 10, 15, 20 and 30 minutes after the DNP-BSA administration, a graph was prepared indicating time in abscissa and the edema thickness in ordinate, and edema thickness AUC up to 2 hours was obtained by calculation according to the following equation.

Edema thickness AUC(mm·minute)=½×10×A+5×(A+B)/2+5×(B+C)/2+10×(C+D)/2  [Equation 5]

A: Edema thickness 10 minutes after DNP-BSA administration

B: Edema thickness 15 minutes after DNP-BSA administration

C: Edema thickness 20 minutes after DNP-BSA administration

D: Edema thickness 30 minutes after DNP-BSA administration

A suppressing ratio on edema of a test compound was obtained by calculation in accordance with the following equation.

Edema suppression ratio(%)=[1−B/A]×100  [Equation 6]

A: Edema thickness AUC of positive control

B: Edema thickness AUC of test compound administered group

(2) Measurement Results

Representative compounds of the objective Compounds (I) described in the specification suppressed the footpad edema caused by IgE stimulation, i.e., footpad edema observed when DNP-BSA was administered to the mice sensitized with the anti-DNP-BSA IgE serum, compared with the positive control group by oral administration of 0.1 to 500 mg/kg.

Therefore, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention exhibit suppressing action on footpad edema caused by IgE antibody, which is an allergic stimulant, and thus they are useful as prophylactic and/or therapeutic drugs for allergic diseases.

5. Suppressing Effect on Mouse Acetic Acid Writhing Reaction (1) Method for Measurement

A suppressing effect on acetic acid writhing reaction, which is an acute pain model, was studied by the following method. Groups of ICR female mice (6-week old) each consisting of eight mice were used for the test. A test compound was suspended or dissolved in purified water containing 0.5% methylcellulose and orally administered to the test animals at 0.1 to 500 mg/10 ml/kg. To the control group, purified water containing 0.5% methylcellulose was administered in a similar manner, which was not added with any test compound. One hour after the administration of the test compound, 0.9% aqueous acetic acid was intraperitoneally administered to the mice in a volume of 5 ml/kg, and number of writhing reactions during 15 minutes immediately after the administration of acetic acid was counted. Suppression ratio relative to the control group was obtained by calculation according to the following equation.

Writhing suppression ratio(%)=[1−B/A]×100  [Equation 7]

A: Writhing number of positive control group

B: Writhing number of test compound administered group

(2) Measurement Results

The representative compounds of the objective Compounds (I) described in the specification suppressed writhing caused by administration of aqueous acetic acid compared with the positive control group at oral administration of 0.1 to 500 mg/kg.

It has been elucidated that a writhing reaction caused by intraperitoneal administration of acetic acid is caused due to production of prostaglandin [Matsumoto et al., European Journal of Pharmacology (Eur. J. Pharmacol), 1998, vol. 352, p. 47; Ueno et al., Biochemical Pharmacology (Biochem. Pharmacol), 2001, vol. 15, p. 157].

Therefore, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention are useful as prophylactic and/or therapeutic agents for acute pain caused by prostaglandins.

6. Prophylactic and Therapeutic Effects for Rat Adjuvant Arthritis (1) Method for Measurement

A suppressing effect on footpad edema observed in rat adjuvant arthritis, which is a disease model of rheumatoid arthritis as being one of autoimmune diseases and also a chronic inflammatory disease, was studied by the following method. Groups of Lewis female rats (8-week old) each consisting of six mice were used for the test. The test animals were immunized by subcutaneously administering, to right hind leg footpads, 50 μl of liquid paraffin containing 10 mg/ml of M. tuberclulosis H37 RA (DIFCO) as an adjuvant. A test compound was suspended or dissolved in purified water containing 0.5% methylcellulose and orally administered to the test animals at 0.1 to 500 mg/5 ml/kg. The test compound was administered twice a day for 14 days, from the 12th day after the immunization. To the control group, purified water containing 0.5% methylcellulose was administered in a similar manner, which was not added with any test compound. Every 2 or 3 days after the administration of adjuvant, volume of left hind leg footpad, which was not administered with the adjuvant, was measured by using an apparatus for measuring a volume of edema of a rat hind leg footpad (Unicom). A suppression ratio on edema was obtained by calculation using the following equation.

Edema suppression ratio(%)={1−[(D−C)/C]/[(B−A)/A]}×100  [Equation 8]

A: Left hind leg footpad volume of positive control immediately before administration of adjuvant

B: Left hind leg footpad volume of positive control on each measurement day

C: Left hind leg footpad volume of test compound administered group immediately before administration of adjuvant

D: Left hind leg footpad volume of test compound administered group on each measurement day

(2) Measurement Results

The representative compounds of the objective Compound (I) described in the specification suppressed footpad edema in adjuvant arthritis compared with the positive control group.

Therefore, the novel substituted phenylalkanoic acid derivatives or salts thereof according to the present invention are useful as agents for prophylactic and/or therapeutic drugs for rheumatoid arthritis and autoimmune diseases.

7. Effect on Rat Pulmonary Fibrosis (1) Method for Measurement

A suppressing effect on pulmonary fibrosing in a bleomycin-induced rat pulmonary fibrosis model, which is a pathological model of pulmonary fibrosis, was studied by the following method. Groups of BN female rats (7-week old) each consisting of seven rats were used for the test. The test animals were anesthetized with ketamine and xylazine, and the tracheae were exposed. Then, a 125 μg/0.1 ml solution of bleomycin (Nippon Kayaku) dissolved in physiological saline (Ohtsuka Pharmaceutical Factory) was injected into the tracheae by using a syringe. The negative control group was administered with 0.1 ml of saline into the tracheae.

Each test compound was suspended or dissolved in purified water containing 0.5% methylcellulose, and orally administered to the test animals at doses of 10, 30, 100 and 300 mg/5 ml/kg. The administration of the test compounds was started from the day of the bleomycin administration and performed once or twice a day for 21 days. The positive control group was administered with purified water containing 0.5% methylcellulose not added with any test compound in a similar manner. On the 21st day after the administration of bleomycin, the rats were sacrificed, and lungs were fixed with neutral buffered formalin to prepare histopathological samples. Staining of the histopathological samples was performed by the Azan method.

The histopathological samples of lungs were examined, and degree of fibrosing was represented with the following scores on the basis of formation of granulation tissues and proliferation of collagen fibers as indicators, i.e., −: no abnormality, ±: extremely mild change, +: mild change, ++: moderate change, and +++: significant change.

(2) Measurement Results

The fibrosing score of the negative control group was minus (−), and no pulmonary fibrosing was observed. The median of the fibrosing score of the positive control group was from ++ to +++, and pulmonary fibrosing was observed. The medians of the fibrosing score of the groups of rats administered with the test compounds (Compound Nos. G-2, G-4 and V-40) were from ± to +, and thus the fibrosing was milder compared with the positive control group. The median of the fibrosing score of the group administered with the other test compounds (Compound Nos. G118 and V-59) was from ± to +, and thus pulmonary fibrosing was milder that that observed in the positive control group. Accordingly, the compounds of the present invention are useful as a prophylactic and/or therapeutic agent for pulmonary fibrosis, and type 4 PLA₂ inhibitor compounds are useful as a prophylactic and/or therapeutic agent (including a progression-preventing agent) for pulmonary fibrosis.

Further, known cPLA₂ inhibitory compounds, arachidonyl trifluoromethyl ketone, 4-(1-benzhydryl-6-chloro-1H-indol-3-ylmethyl)-3-methoxybenzoic acid, N-{1-[2-(2,4-difluorobenzoyl)benzoyl]-4-tritylsulfanylpyrrolidin-2-ylmethyl}-4-(2,4-dioxothiazolidin-5-ylidenemethyl)benzoic acid amide and 4-{4-[2-(2-[bis(4-chlorophenyl)methoxy]ethylsulfonyl)ethoxy]phenyl}-1,1,1-trifluoro-2-butanone, are intraperitoneally or orally administered in a similar manner. Fibrosing is mild also in the groups administered with these known type 4 PLA₂ inhibitory compounds.

INDUSTRIAL APPLICABILITY

The compounds of the present invention have superior suppressing action on prostaglandin production and leukotriene production, and they are useful as active ingredients of medicaments for prophylactic and/or therapeutic treatment of various inflammatory diseases, autoimmune diseases, allergic diseases, pain, fibrosis and the like caused by these lipid mediators. 

1. A compound represented by the following formula (II):

in the formula, each of C²′, C³′, C⁴′, C⁵′, and C⁶′ in the aromatic ring (E′) represents a ring-constituting carbon atom, any one of them to which Rs′ and G does not bind may be replaced with V′, V′ represents nitrogen atom, or carbon atom substituted with Zx′, Zx′ has the same meaning as Zx mentioned above, provided that when Zx contains hydroxyl group, the hydroxyl group may be protected with Rp¹, and when Zx contains amino group, the amino group may be protected with Rp², Rs′ represents -D-Rx′ or —N(Ry′)(Rz′), -D-Rx′ and —N(Ry′)(Rz′) have the same meanings as -D-Rx and —N(Ry)(Rz), respectively, provided that when -D-Rx or —N(Ry)(Rz) contains hydroxyl group, the hydroxyl group may be protected with Rp¹, when -D-Rx or —N(Ry)(Rz) contains amino group, the amino group may be protected with Rp², G represents chlorine atom, bromine atom, iodine atom, mesylate group, triflate group, or an arenesulfonate group of which aromatic portion may be substituted with one of T¹ or two or more of the same or different T¹, and Y′ represents a lower alkyl group having 1 to 4 carbon atoms.
 2. The compound according to claim 1, wherein, in the formula (II), n is an integer of 2, G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with —N(Rn¹)(Rn²) group (provided that one of Rn¹ and Rn² is a substituent other than hydrogen atom), C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′.
 3. The compound according to claim 1, wherein, in the formula (II), n is an integer of 2, C³′ is carbon atom to which G binds, C⁴′ is carbon atom to which Rs′ binds, C⁵′ is carbon atom substituted with Zx′, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Zx′ is N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N,N-dimethylamino group, N,N-diethylamino group, formylamino group, acetylamino group, carbamoylamino group, mesylamino group, or N,N-dimethylsulfamoylamino group, provided that when Zx′ contains amino group, the amino group may be protected with Rp², Rs′ is —O-Rx′, Rx′ is butyl group, isobutyl group, 2-ethylbutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, indan-2-yl group, 4-methylindan-2-yl group, 5-methylindan-2-yl group, 4,7-dimethylindan-2-yl group, 5,6-dimethylindan-2-yl group, 4-fluoroindan-2-yl group, 5-fluoroindan-2-yl group, 4,7-difluoroindan-2-yl group, 5,6-difluoroindan-2-yl group, 4-chloroindan-2-yl group, 5-chloroindan-2-yl group, 4,7-dichloroindan-2-yl group, 5,6-dichloroindan-2-yl group, 4-methoxyindan-2-yl group, 5-methoxyindan-2-yl group, 4,7-dimethoxyindan-2-yl group, 5,6-dimethoxyindan-2-yl group, 1-phenylethyl group, 1-(2-fluorophenyl)ethyl group, 1-(3-fluorophenyl)ethyl group, 1-(4-fluorophenyl)ethyl group, 1-(2-chlorophenyl)ethyl group, 1-(3-chlorophenyl)ethyl group, 1-(4-chlorophenyl)ethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2,3-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 4-chlorophenylmethyl group, 2,3-difluorophenylmethyl group, 2,4-difluorophenylmethyl group, 2,5-difluorophenylmethyl group, 3,4-difluorophenylmethyl group, 2,3-dichlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 2,5-dichlorophenylmethyl group, 2,6-dichlorophenylmethyl group, 3,4-dichlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 3,6-dichlorophenylmethyl group, 2-(trifluoromethyl)phenylmethyl group, 3-(trifluoromethyl)phenylmethyl group, 4-(trifluoromethyl)phenylmethyl group, 2-(2-methylphenyl)ethyl group, 2-(3-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2-methoxyphenyl)ethyl group, 2-(3-methoxyphenyl)ethyl group, 2-(4-methoxyphenyl)ethyl group, 2-(2-fluorophenyl)ethyl group, 2-(3-fluorophenyl)ethyl group, 2-(4-fluorophenyl)ethyl group, 2-(2-chlorophenyl)ethyl group, 2-(3-chlorophenyl)ethyl group, 2-(4-chlorophenyl)ethyl group, 2-[2-(trifluoromethyl)phenyl]ethyl group, 2-[3-(trifluoromethyl)phenyl]ethyl group, 2-[4-(trifluoromethyl)phenyl]ethyl group, 2-[4-(N,N-dimethylamino)phenyl]ethyl group, 2-phenyloxyethyl group, 2-(2-chlorophenyloxy)ethyl group, 2-(3-chlorophenyloxy)ethyl group, 2-(4-chlorophenyloxy)ethyl group, 2-(phenylthio)ethyl group, 2-(N-phenyl-N-methylamino)ethyl group, or 2-(N-ethyl-N-phenylamino)ethyl group, G is bromine atom or iodine atom, and Y′ is methyl group or ethyl group.
 4. The compound according to claim 1, wherein, in the formula (II), G binds to C³, in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is a ring-constituting carbon atom substituted with Zx′, or an unsubstituted ring-constituting carbon atom, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, Rs′ is —O-Rx′, and Rx′ is a linear or branched saturated alkyl group having 3 to 8 carbon atoms, or Ra or Rb.
 5. The compound according to claim 1, wherein, in the formula (II), n is an integer of 2, G binds to C³′ in the aromatic ring (E′), Rs′ binds to C⁴′ in the aromatic ring (E′), C⁵′ is carbon atom substituted with nitro group, C²′ and C⁶′ are unsubstituted ring-constituting carbon atoms, and Rs′ is —O-Rx′. 